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Resources

Tools, checklists and straight answers

Everything on this page is free and requires no email address. If something here saves you a phone call, that is the point of it.

Checklist 01

Entity selection: the eight questions that matter

“Should I be an S-corp?” has no general answer. It has eight specific ones. Work through these before anyone quotes you a saving.

  • What is your net profit after paying yourself?Below roughly $80,000–$100,000 the extra cost of an S-corp (payroll, a separate return, higher preparation fees) frequently exceeds the self-employment tax saved.
  • What would you have to pay someone else to do your job?That is your reasonable compensation floor. If the honest answer absorbs most of the profit, there is little left to distribute and little to save.
  • Do you have employees, and what is the payroll?W-2 wages feed the Section 199A limitation at higher income levels. Entity choice changes the wage base, which can decide whether the QBI deduction survives.
  • Are you profitable, or generating losses?Losses behave very differently. S-corp basis rules are stricter than partnership rules, and a loss you cannot deduct this year has a real cost.
  • How many owners, and are any of them entities or non-residents?S-corps have hard eligibility limits: 100 shareholders, one class of stock, no corporate or non-resident alien shareholders. Failing one of these ends the election.
  • Will the business hold appreciating assets?Real estate inside an S-corp is difficult to remove without triggering gain. A partnership or LLC is usually the better home for appreciating property.
  • When do you expect to sell, and to whom?Buyers usually want an asset purchase; sellers usually want stock. Entity form drives which is available and what it costs. Section 1202 requires C-corporation status from issuance.
  • Which states will you operate in?Some states do not recognize the S-election, or impose entity-level taxes on pass-throughs. A structure that is efficient in Florida can be poor in California or New York City.

Checklist 02

Year-end planning: still open, already closed

The value of Q4 planning is knowing which list an item is on. Working on something from the second list is wasted effort.

Still open in Q4

  • Place assets in service before 31 December to claim depreciation this year: delivery is not enough, they must be ready and available for use
  • Establish and fund a qualified retirement plan; some plan types must be adopted by year-end even if funded later
  • Review accounts receivable and write off genuinely uncollectible balances
  • Accelerate deductible expenses or defer income where the rate arithmetic supports it
  • Harvest capital losses to offset realized gains, watching the wash sale rules
  • Make charitable contributions, using appreciated securities rather than cash where possible
  • Confirm shareholder basis before taking a distribution that could otherwise be taxable
  • Pay accrued bonuses to non-related parties within the permitted window after year-end
  • Take required minimum distributions if you have reached the applicable age
  • Reconcile reasonable compensation and run a final payroll adjustment if needed

Already closed by then

  • Most entity elections for the current year: Form 2553 has a 15 March deadline for the year in progress
  • Retirement plan adoption for certain plan types that require establishment during the year
  • Section 83(b) elections, which run 30 days from grant and cannot be extended
  • 1031 exchange identification, which is 45 days from the relinquished-property closing
  • Anything requiring a transaction to have occurred: the tax year is a hard boundary
Dates shift. Deadlines move when they fall on a weekend or federal holiday, and the IRS postpones them in declared disaster areas, which affects Florida more often than most states. Check the current date before you rely on it.

Checklist 03

IRS notice decoder

The code in the top-right corner tells you what the letter is and how long you have. Response windows on the last two cannot be extended.

Common IRS notice codes, what they mean and the response window for each
NoticeWhat it isWindowWhat to do
CP14 Balance due, first notice 21 days The opening notice for an unpaid balance. Verify it before paying; it is frequently generated before a payment has been applied.
CP2000 Proposed change from document matching 30 days An automated mismatch between your return and third-party forms. Often wrong. Responding on time preserves your right to dispute.
CP2501 Earlier-stage document mismatch 30 days A softer precursor to a CP2000. Easier to resolve at this stage than after a proposal is issued.
CP161 Balance due, business 10 days The business equivalent of a CP14, typically following an underpaid return.
CP136 Deposit schedule change n/a Notifies a change to your Form 941 deposit frequency based on the lookback period. Ignoring it causes deposit penalties.
CP504 Notice of intent to levy 30 days A serious escalation. The IRS may levy state refunds and is signalling further collection action.
LT11 / Letter 1058 Final notice of intent to levy 30 days Triggers your right to a Collection Due Process hearing. Requesting one suspends collection. This deadline matters enormously.
Letter 525 / 692 Examination report 30 days The examiner's proposed adjustments. Thirty days to agree or to protest to Appeals.
Letter 3219 / CP3219A Statutory notice of deficiency 90 days The 90-day letter. The only route to Tax Court, and the window cannot be extended for any reason.

Let's look at your next filing season before it arrives.

A 30-minute review is usually enough to tell you whether you are leaving money on the table, carrying compliance risk, or both.