Most people who hire a CPA to prepare their tax return have already tried doing it themselves with software, or have used a chain preparer, or have a CPA they’re not particularly happy with. The reasons clients move to me are usually some version of: the situation got too complicated for software to handle without producing wrong answers; an audit or notice arrived and they realized the return that triggered it wasn’t done as carefully as they assumed; or they want a preparer who’s actually thinking about the return rather than running it through a checklist.

I’m Lawrence Israeloff. I’m a tax attorney and a CPA, and I’ve been preparing returns for clients across Long Island and the New York City metro for over two decades. The returns I prepare aren’t the simplest ones – clients with W-2 income and standard deductions are usually fine with software. The returns that justify professional preparation are the ones where the right answer isn’t obvious from the documents.

Where return preparation actually goes wrong

Software does a competent job of arithmetic. What it doesn’t do well, and what generic preparers often miss, is judgment about how to report things. A few patterns I see when reviewing returns that were prepared elsewhere:

  • Misclassified income. Whether something is wages, self-employment income, royalty income, capital gain, or non-taxable return of capital often depends on facts the form itself doesn’t capture. A 1099-MISC with an amount in box 3 (other income) versus box 7 (formerly nonemployee compensation, now reported on 1099-NEC) versus box 1 of a 1099-K can produce three different tax results from the same dollar received. The right classification often requires knowing what the underlying transaction actually was.
  • Missed basis tracking. Cost basis for investments, real estate, partnership interests, and inherited property can be the largest single source of overpaid tax on a return. Brokerages report basis for covered securities but not always correctly for stock acquired through ESPPs, ISOs, or RSUs. Inherited property gets a stepped-up basis that often isn’t reflected anywhere on a Form 1099. K-1 partners need to track outside basis themselves because the partnership doesn’t track it for them. When basis is wrong on the upside, the taxpayer overpays; when it’s wrong on the downside, the taxpayer creates an IRS problem they don’t know about yet.
  • Improper handling of K-1s. Partnership and S-corp K-1s carry information that affects multiple parts of a return – passive activity losses, qualified business income, basis adjustments, foreign tax credits, alternative minimum tax preferences, state-level reporting differences. K-1s that arrive late or with errors often get plugged in incompletely by preparers under deadline pressure. The result is returns that miss deductions, miscalculate QBI, or fail to track suspended losses correctly.
  • State residency and sourcing errors. New York is among the most aggressive states on residency questions, and clients who split time between NY and another state (Florida most commonly) frequently have returns prepared without careful attention to day counts, the statutory residency rules, the convenience-of-the-employer rule for telecommuters, or the proper sourcing of income across states. A return that ignores these issues isn’t necessarily wrong by software standards, but it’s wrong by NY DTF standards if the state ever looks closely.
  • Trust and estate filings done as afterthoughts. Form 1041 returns for trusts and estates have their own quirks – distribution deduction calculations, fiduciary accounting income versus taxable income, allocation of expenses between principal and income, K-1 reporting to beneficiaries, and the timing of elections that have to be made on the first return filed. These returns are often handled by preparers who don’t see many of them, and the results show.

What you actually get from professional preparation

The deliverable isn’t just the return. It’s the work that produces a return I’d be willing to defend to the IRS or NY DTF if asked. Concretely, that includes:

  • A pre-filing review of the prior year’s return to identify carryforwards (capital losses, charitable contribution carryovers, NOLs, basis adjustments, suspended passive losses, AMT credits) that need to flow to the current year. Most return-to-return errors compound when these get dropped.
  • A judgment call on every reporting position that isn’t mechanical – how to characterize a transaction, when to take an aggressive but defensible position versus a conservative one, how to disclose adequately when disclosure protects against penalties, and where to leave room for explanation if the IRS asks.
  • Coordination with the rest of the client’s planning. If we did a Roth conversion in November, the return needs to reflect it. If a property was sold under a §1031 exchange, the basis carries over and the form needs to be filed. If the client made a §475(f) trader election, the return reports it differently. The preparer needs to know what was done during the year and report it accordingly.
  • A clear communication of what’s on the return and why. Clients should understand their own returns. I walk through the meaningful items, flag anything that’s likely to draw IRS attention, and explain what the return implies for next year’s planning.

Returns I prepare regularly

The categories that make up most of the practice: individual returns (Form 1040) for high-income clients with multi-source income, equity compensation, investment activity, real estate, multi-state issues, or self-employment; pass-through entity returns (Form 1065 partnerships, Form 1120S S-corps) for closely-held operating businesses, professional practices, and real estate entities; corporate returns (Form 1120) for C-corps, including those with multi-state nexus or international issues; fiduciary returns (Form 1041) for trusts and estates, including grantor trust filings, complex non-grantor trusts, charitable remainder trusts, and estate income tax during administration; and gift tax returns (Form 709) when lifetime gifting strategies require reporting.

Less common but in scope when needed: estate tax returns (Form 706) for taxable estates, foreign account reporting (FBAR/FinCEN 114, Form 8938), and amended returns when prior-year errors need to be corrected.

Year-round compliance, not just filing season

Return preparation is the visible part of compliance, but it’s not the whole job. The supporting work happens throughout the year:

  • Quarterly estimated tax calculations for clients without sufficient withholding – most business owners, retirees with substantial investment income, and high-earners with stock-based compensation. Underpayment of estimated tax is a common and unnecessary penalty issue.
  • Safe harbor analysis – whether to base estimated payments on prior-year tax or current-year projection, whether the higher-income safe harbor (110% of prior year for AGI over $150K) applies, and how to time payments to avoid penalty calculations.
  • Tracking of carryforward items and elections that affect future returns – capital losses, NOLs, charitable carryovers, suspended passive losses, AMT credit carryovers, basis adjustments, §163(j) interest carryovers.
  • Coordination with retirement plan deadlines (SEP-IRA, solo 401(k), defined benefit plan funding) that affect both this year’s deductions and future planning.
  • Monitoring of changes in IRS guidance and New York State tax law that affect the client’s specific situation, with notice when something requires action before year-end.

Who I work with most often

The recurring patterns: high-income individuals and couples whose returns are too complex for software but who don’t want a chain preparer; closely-held business owners who need both the entity return and their personal return prepared by someone who sees the whole picture; professional practices, real estate investors, and other clients with K-1 income from multiple sources; trustees and executors handling fiduciary returns during the administration of trusts and estates; and clients who’ve received an IRS or NY DTF notice and need a preparer who can both fix the return and respond to the inquiry.

If your situation is W-2 income, standard deduction, no investments to speak of, and no business interests – software is genuinely fine, and I’ll tell you that.

Long Island, NYC, and the surrounding metro

I work out of Melville, NY and prepare returns for clients across Long Island, the five boroughs, Westchester, and the broader New York metro, plus clients who’ve relocated out of state but maintain NY filing obligations. New York’s tax structure (the state’s residency rules, NYC’s separate income tax for residents, the state’s pass-through entity tax election, the various local taxes and surcharges) adds genuine complexity that out-of-state preparers often handle poorly.

Let's talk

If you’re rethinking your current preparation arrangement, dealing with a return that’s gotten too complicated for the tool you’ve been using, or facing an issue that surfaced after a return was filed, that’s typically when this conversation makes sense. Schedule a consultation and we’ll talk through what you have and where the gaps are.

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