Tax Preparation Is Not Just Compliance It's the Final Step in a Planning Process
A tax return is a legal document. It reports positions on income, deductions, elections, and credits that can be questioned, audited, and potentially litigated. The quality of a return is not measured only by whether it is filed on time and avoids penalties. It is measured by whether the positions taken are accurate, defensible, and reflective of the best available treatment of the client's facts under the law.
Most tax preparers are compliance-focused: they receive documents, enter data, and produce a return. That produces an accurate return in the sense that the numbers match the documents. But it does not produce an optimal return one that takes every available deduction, makes every available election, allocates income correctly across entity and individual returns, and identifies positions that might be reported differently with better documentation.
At Montgomery Legal, return preparation is inseparable from the planning work done throughout the year. Every return is prepared by the same advisor who understands the client's business structure, their planned transactions, and the planning decisions made during the year not a separate preparer seeing the situation for the first time in March. Elections are intentional. Deductions are documented. K-1 allocations are consistent across entity and individual returns. And every return is reviewed for positions that a subsequent audit would need to explain.
Why the attorney credential matters in return preparation: Tax positions taken on a return can be subject to accuracy-related penalties if they lack substantial authority. The analysis of whether a position has substantial authority and whether it should be disclosed on the return is a legal analysis, not just an accounting one. An attorney-CPA who prepares the return is better positioned to evaluate and document borderline positions than a preparer who cannot practice law.
Individual Income Tax Returns
Individual returns range from relatively straightforward W-2-based returns to highly complex filings involving business ownership, multiple pass-through entities, investment portfolios, real estate, stock compensation, trust distributions, and multi-state income. We prepare individual returns across the full spectrum of complexity, with particular depth in returns involving business ownership, capital transactions, and the interaction between individual and entity-level reporting.
The federal individual income tax return covers all income sources wages, self-employment, pass-through business income, investment income, rental income, retirement distributions, and more along with the deductions, credits, and elections that reduce the resulting liability. For business owners, the individual return is the endpoint of a chain that runs through one or more entity-level returns and reflects decisions made throughout the year.
We prepare complex individual returns involving Schedule C (sole proprietorship), Schedule D (capital gains and losses), Schedule E (rental and pass-through income), self-employment tax, net investment income tax, alternative minimum tax analysis, and the interaction of multiple K-1s from S-Corps, partnerships, and trusts. Basis tracking, passive activity loss management, and at-risk limitation analysis are addressed as part of the preparation rather than left to the client to reconcile.
- Business owners with S-Corp or partnership K-1s
- Real estate investors with depreciation and PAL tracking
- Stock compensation RSUs, ISOs, NSOs, and ESPP
- Installment sale reporting across multiple years
- Roth conversion income and QBI interaction
- Multi-state returns for Texas residents with out-of-state income
- High-income returns subject to NIIT and additional Medicare tax
- Final individual returns for decedents
Business Tax Returns
Business returns are not standalone documents they flow through to the owners' individual returns via K-1s and must be prepared in coordination with the individual filings to ensure consistency. Errors or omissions in the entity return generate K-1s that create problems downstream, and positions taken in the entity return need to be defensible at both the entity and individual levels. We prepare entity and individual returns for the same client in the same engagement, which eliminates the coordination gap that causes most entity-level preparation errors.
The S-Corp return reports entity-level income, deductions, credits, and separately stated items and generates Schedule K-1s for each shareholder allocating their pro-rata share. The return must track the accumulated adjustments account (AAA), other adjustments account, and each shareholder's stock and debt basis all of which affect the taxability of distributions and the deductibility of losses.
We prepare Form 1120-S in coordination with the shareholders' individual returns, ensuring that shareholder basis is tracked correctly, that reasonable compensation is properly reported, and that the return is consistent with the shareholders' K-1s. Separately stated items Section 179 deductions, charitable contributions, investment interest, and others are allocated correctly and reconciled to the individual returns.
- AAA and OAA tracking for distribution characterization
- Shareholder stock and debt basis calculations
- Reasonable compensation documentation and reconciliation
- Built-in gains tax for entities converting from C to S status
- QBI deduction optimization at shareholder level
The partnership return is among the most technically complex in the federal tax system. Partnerships can make special allocations of income, deductions, and credits among partners subject to the substantial economic effect requirements of §704(b). They involve outside basis and capital account tracking, §754 step-up elections, guaranteed payments, and potentially complex §704(c) and §743(b) adjustments when partners join or exit at values different from their inside basis.
We prepare partnership returns for multi-member LLCs, investment partnerships, real estate partnerships, family limited partnerships, and professional services partnerships with K-1s that correctly reflect each partner's allocable share of all income, loss, deduction, and credit items. Capital account reconciliation and outside basis tracking are maintained from year to year, not reconstructed annually.
- §704(b) capital account maintenance (tax basis method)
- §704(c) built-in gain/loss allocations
- §754 optional basis adjustment elections
- Guaranteed payment reporting and characterization
- Self-employment income determination for general partners
- Real estate partnerships with depreciation and §1031 activity
C-corporations are taxed at the entity level currently at a flat 21% federal rate before any after-tax profits are distributed to shareholders as dividends. The C-Corp return tracks earnings and profits, net operating losses, dividends received deductions, and tax credits. For closely held C-Corps, accumulated earnings tax exposure, personal holding company status, and reasonable compensation for shareholder-employees are all considerations that affect return preparation.
We prepare Form 1120 for closely held and family-owned C-Corps, including the annual analysis of distributions to ensure they are not recharacterized as constructive dividends, and the coordination with shareholder W-2s to document reasonable compensation. For C-Corps that have recently converted from S-Corp status, we track built-in gains recognition and the S-Corp earnings and profits account.
- Accumulated earnings tax analysis and documentation
- Reasonable compensation for shareholder-employees
- NOL carryforward tracking and utilization
- QSBS (§1202) exclusion eligibility tracking
- Earnings and profits calculation for distribution characterization
Trust and Estate Tax Returns
Fiduciary income tax returns are a specialized area that most general practitioners prepare infrequently and often without a full command of the technical rules governing distributable net income, the distribution deduction, the separate share rule, and the interaction between the trust's tax liability and the beneficiaries' individual returns. We prepare these returns as a regular part of our practice, in coordination with the trust administration and estate administration engagements where applicable.
Irrevocable trusts and estates that earn income must file Form 1041 for each tax year in which they have taxable income of $600 or more. Trusts are taxed at extremely compressed rates the highest federal bracket (37%) applies to income above just $15,200 in 2024 which makes the distribution deduction and the timing of distributions one of the most significant planning variables in trust administration.
The distribution deduction allows the trust to deduct income distributed to beneficiaries, shifting the tax liability from the trust (with its compressed rates) to the beneficiary (who is typically taxed at lower individual rates). But distributions must carry out distributable net income (DNI) in the correct order and character and the K-1s step-cardd to beneficiaries must accurately reflect the character of the income distributed. Errors in DNI calculation or K-1 preparation create problems at the beneficiary level that are difficult to correct after the fact.
- DNI calculation and distribution deduction optimization
- Character tracing of distributed income for K-1 reporting
- Grantor trust reporting statements (no separate 1041 filing)
- Separate share rule for trusts with multiple beneficiaries
- Estate income tax returns from date of death through closing
- 65-day rule elections for estates and complex trusts
- Final year deductions and excess deduction pass-through
The federal estate tax return (Form 706) is required for estates that exceed the applicable exclusion amount $13.61 million per individual in 2024 and is due nine months after the date of death with a six-month extension available. We also file Form 706 for qualifying estates below the threshold when a portability election is desired, preserving the deceased spouse's unused exemption for the surviving spouse's estate.
Form 709, the annual gift tax return, is required whenever taxable gifts exceed the annual exclusion amount, when gift-splitting is elected between spouses, or when gifts are made to irrevocable trusts or under certain other circumstances even if no tax is due. Consistent, accurate 709 filing across years maintains the running account of lifetime exemption used a record that matters when the estate tax return is eventually filed.
- 706 portability elections for all eligible married decedents
- Closely held business interest valuation discounts
- Marital and charitable deduction elections
- §6166 installment payment elections for illiquid estates
- 709 filing for gifts to SLATs, IDGTs, GRATs, and other irrevocable trusts
- Gift-splitting elections and cumulative exemption tracking
Non-Profit and Tax-Exempt Organization Returns
Tax-exempt organizations are not exempt from all tax obligations and they are not exempt from compliance requirements that can result in penalty excise taxes, loss of exemption, and public reputational harm if ignored. The Form 990 family of returns is a public document, reviewed by donors, watchdog organizations, and state attorneys general. What it says and how it says it matters beyond mere compliance.
The Form 990 is an annual information return not an income tax return that reports the organization's income, expenses, programs, governance, compensation of officers and key employees, and transactions with related parties. It is filed publicly and is available to anyone who requests it. The narrative portions of the 990 program accomplishments, mission descriptions, and governance disclosures are as important as the financial schedules, and a poorly drafted 990 can undermine donor confidence even when the organization's finances are sound.
We prepare Form 990 (for organizations with gross receipts over $200,000 or total assets over $500,000), Form 990-EZ (for smaller organizations), and Form 990-PF (for private foundations). For organizations with unrelated business income, we prepare Form 990-T as well ensuring that UBIT is correctly identified, computed, and reported, and that the organization is not inadvertently converting exempt activities into taxable ones.
- Form 990, 990-EZ, 990-PF, and 990-T preparation
- Unrelated business income identification and UBIT computation
- Compensation reporting for officers and key employees
- Related party transaction disclosure (Schedule L)
- Program accomplishment and mission narrative
- Private foundation excise tax computation and planning
- Automatic revocation risk assessment for organizations behind on filing
Three-year automatic revocation: A tax-exempt organization that fails to file a required annual return for three consecutive years loses its tax-exempt status automatically without IRS action or notice. Reinstatement is possible but requires a formal application and may not be retroactive. Organizations that have lapsed in filing should not simply file the missing returns without first assessing whether automatic revocation has already occurred and whether retroactive reinstatement is available.
Filing Deadlines and Extensions
Federal tax filing deadlines are staggered by entity type and tax year. Missing a deadline without an extension creates failure-to-file penalties which are among the most expensive penalties in the tax code and often dwarf the underlying tax liability for businesses with substantial income. Understanding which deadlines apply, and what an extension does and does not accomplish, is basic compliance hygiene.
Partnerships and S-Corporations
- Form 1065 (partnership return) due
- Form 1120-S (S-Corp return) due
- S-Corp election deadline for current year (Form 2553)
- Extension to September 15 available (Form 7004)
Individuals, Trusts, and C-Corporations
- Form 1040 (individual return) due
- Form 1041 (trust/estate return) due
- Form 1120 (C-Corp, calendar year) due
- Form 709 (gift tax return) due
- Q1 estimated tax payment due (individuals)
- Extension to October 15 available for 1040 (Form 4868)
Tax-Exempt Organizations
- Form 990, 990-EZ, and 990-PF due (calendar year organizations)
- Form 990-T (unrelated business income) due
- Automatic 6-month extension available (Form 8868)
- Missing 3 consecutive years triggers automatic revocation
Federal Estate Tax Return
- Form 706 (estate tax return) due for taxable estates
- Form 706 due for portability elections (even if no tax owed)
- 6-month extension available does not extend payment deadline
- Missing portability deadline is permanent and irrecoverable
Estimated Tax Payments
- April 15 Q1 payment (January–March income)
- June 15 Q2 payment (April–May income)
- September 15 Q3 payment (June–August income)
- January 15 Q4 payment (September–December income)
- Safe harbor: 100% of prior year tax (110% if AGI over $150K)
Payroll Tax Filings
- Form 941 quarterly (April 30, July 31, Oct 31, Jan 31)
- Form 940 annual FUTA return (January 31)
- W-2s and 1099s January 31 to recipients and SSA/IRS
- Federal tax deposits varies by deposit schedule
Extensions extend the filing deadline not the payment deadline. An extension gives additional time to file the return without penalty, but any tax owed is still due on the original deadline. Underpayment interest accrues from the original due date regardless of whether an extension is in place. For clients with significant year-end income, we calculate estimated liability before filing the extension to ensure any balance due is paid on time.
step-cards We Find in Returns Prepared Elsewhere
When clients come to us after having returns prepared by a prior preparer, the same categories of errors and omissions appear repeatedly. These are not fraud they are the predictable consequence of preparers who lack the depth of knowledge to identify what they are missing, or who lack the planning relationship to know what decisions were made during the year. Below are the step-cards we find most consistently.
S-Corp shareholder basis not tracked losses claimed in excess of basis
S-Corp losses are deductible only to the extent of the shareholder's basis in stock and debt. Many preparers report the K-1 loss without analyzing whether the shareholder has sufficient basis to claim it. Excess losses are suspended and carried forward but only if they are tracked. Losses claimed without adequate basis are disallowed on audit with interest and penalties.
Reasonable compensation not analyzed or documented for S-Corp owners
The IRS requires S-Corp owner-employees to receive a reasonable salary for services rendered. Preparers who accept whatever salary the client paid without analysis or who prepare the return without knowing what salary was paid expose the client to recharacterization of distributions as wages, back payroll taxes, and penalties. We maintain a reasonable compensation analysis in every S-Corp client's file.
Passive activity losses not tracked or correctly classified
Losses from rental activities and passive business investments are deductible only against passive income unless the taxpayer qualifies as a real estate professional or meets the active participation standard. Many returns improperly deduct passive losses against ordinary income, or fail to carry forward suspended losses when the activity is later disposed of. Proper passive activity tracking requires maintaining activity-level records across multiple years.
QBI deduction not optimized or incorrectly calculated
The §199A deduction involves an analysis of business type, taxable income relative to thresholds, W-2 wages, and qualified property that many preparers either skip or compute incorrectly. SSTB limitations, the wage and capital limitation, and the interaction with retirement plan contributions all affect the available deduction. An incorrect QBI calculation can easily understate a deduction worth $20,000–$50,000 or more for a profitable small business.
Missed elections that cannot be made retroactively
The tax code contains numerous elections that must be made on a timely filed return the §754 basis adjustment election, the S-Corp election (Form 2553), installment sale reporting, §1031 exchange reporting, and others. Many of these are irrevocable once the filing window has closed. A preparer who does not know which elections are available or does not communicate with the client before the deadline permanently forecloses planning options that were available at the time of filing.
Form 706 portability election missed after spouse's death
A surviving spouse who does not file Form 706 for the deceased spouse's estate even when no estate tax is owed permanently loses the ability to use the deceased spouse's unused exemption. At the current exemption level, this is a $13+ million planning opportunity. After the 2025 sunset, it will still be a $7+ million opportunity. Preparers who do not know the portability rules, or who do not communicate with estate attorneys, routinely let this deadline pass without action.
Our Preparation Process
The quality of a return depends not just on the preparer's knowledge but on the information-gathering process that precedes preparation. A return is only as good as the underlying data and that data requires an organized intake process, proactive communication about what is needed, and a review that catches errors before the return is filed rather than after.
Engagement and Document Intake
We establish the scope of the engagement and provide a tailored document request list specific to the entity type, the prior year return, and any planning activities that occurred during the year. We do not use generic checklists that generate documents we do not need and miss documents we do. The intake is organized to minimize client burden while ensuring completeness.
Prior Year Review and Continuity Check
For new clients, we review the prior year return before beginning preparation. This identifies carryforward items NOLs, passive activity losses, suspended basis limitations, capital loss carryovers that must be incorporated into the current year return. It also surfaces positions that may have been taken incorrectly in the prior year and that we need to evaluate before continuing.
Transaction and Planning Reconciliation
Before preparing the return, we reconcile the documents received against the planning decisions made during the year. Retirement plan contributions, S-Corp distributions, significant capital transactions, installment payments received, trust distributions, and other events are verified and confirmed before they are entered into the return. Discrepancies are identified and resolved before filing not discovered on audit.
Preparation, Elections, and Positions
The return is prepared with all applicable elections evaluated not defaulted. Where a taxpayer-favorable election is available and appropriate, it is made. Where a position is taken that requires disclosure (under Regulation §1.6662-3), the disclosure statement is prepared. Interrelated returns entity and individual are prepared in coordination, not sequentially with the individual return prepared from the entity return without review.
Review, Client Communication, and Delivery
Every return is reviewed before it goes to the client. The review focuses not only on accuracy but on audit exposure positions that are unusual, large, or likely to draw IRS attention are examined for documentation and support before the return is filed. We communicate the key figures and any notable positions to the client before filing, so there are no surprises and any questions are resolved before the return is submitted.
Filing, Confirmation, and Planning Handoff
Returns are filed electronically with confirmation of acceptance. Any year-end planning observations matters to address before the next filing year are documented and communicated to the client as part of the filing process. The return is not the end of the engagement; it is the beginning of the next year's planning cycle.
