Tax Prep Checklist

Everything to gather before you file.

Ten minutes of gathering now saves a week of back-and-forth in March. Find your filer type below, pull the documents on the list, and upload them to your Harbor Tax portal as they arrive — we handle the rest.

By Filer Type

Find your list. Most people need two.

W-2 Employee

Employees & households

The simplest file — but the one where credits get missed most often. Bring these and we can usually turn your return around in under a week.

  • All W-2s (every employer, even the two-week job)
  • Prior year tax return, if we didn’t prepare it
  • 1098 mortgage interest statement and property tax bills
  • Childcare provider name, EIN, and amount paid (for the credit)
  • 1098-T tuition statements and student loan interest (1098-E)
  • Records of any life changes — marriage, new dependent, home purchase, relocation to Florida
  • HSA contributions and distributions (5498-SA / 1099-SA)
Self-Employed

Freelancers, contractors & Schedule C

The highest-stakes category — this is where good records turn directly into lower tax. If you use QuickBooks or Xero, read access replaces most of this list.

  • All 1099-NEC and 1099-K forms, plus records of income not on a 1099
  • Expense records by category: software, supplies, contract labor, insurance
  • Home office square footage and total home square footage
  • Vehicle mileage log or total business miles for the year
  • Health insurance premiums paid out of pocket
  • Quarterly estimated tax payments made (dates and amounts)
  • Retirement contributions — SEP-IRA, Solo 401(k), traditional IRA
Investor

Brokerage, crypto & K-1s

The paperwork arrives late and in waves — consolidated 1099s are often corrected into March. We track what’s outstanding so nothing files early and amends later.

  • Consolidated 1099 from every brokerage (1099-B, 1099-DIV, 1099-INT)
  • Cost basis for anything sold that your broker didn’t report
  • Crypto exchange transaction history — every platform, every trade
  • Schedule K-1s from partnerships, S-Corps, or trusts (these arrive as late as September)
  • Records of worthless securities or capital loss carryforwards
  • 1099-R for retirement account distributions or Roth conversions
Landlord

Rental property owners

Every Tampa duplex and Airbnb has a depreciation schedule hiding in it. First year with us? Bring the closing statement — we rebuild the schedule from scratch.

  • Rent received per property (rent roll or bank deposits)
  • Mortgage interest (1098) and property tax bills per property
  • Insurance, HOA dues, repairs, and management fees
  • Closing statement (ALTA/HUD-1) for any property bought, sold, or refinanced
  • Prior depreciation schedules, if another firm prepared last year’s return
  • Mileage to and from properties, plus travel for out-of-area rentals
  • Short-term rental night counts (Airbnb/VRBO) — it changes the tax treatment

Mark the Calendar

The deadlines that actually matter.

January 31Employers and clients must send W-2s and 1099s. If something hasn’t arrived by mid-February, tell us — we’ll chase it.
March 16S-Corp (1120-S) and partnership (1065) returns due. Miss it without an extension and the penalty is per-partner, per-month.
April 15Individual returns (1040) and payment due. An extension moves the filing deadline — not the payment. Q1 estimated payment is also due today.
June 15 & Sept 15Q2 and Q3 estimated tax payments for the self-employed. September 15 is also the extended deadline for business returns.
October 15Final deadline for extended individual returns. There is no extension beyond this one — get us documents by September 15 to file comfortably.

How It Works

From first upload to e-file.

1

Upload once

You get a secure client portal link — photograph or drag in documents as they arrive. No email attachments, no office drop-off required.

2

We reconcile

Your named CPA or EA checks your file against last year and against IRS records, then sends one consolidated list of anything missing — not fifteen one-off emails.

3

Review together

Before anything is filed you get a draft return and a 15-minute call (or a plain-English summary) explaining what changed from last year and why.

4

E-file & plan

We e-file federal and state, confirm IRS acceptance, and flag next year’s moves — estimated payments, S-Corp election, retirement contributions — while the numbers are fresh.

Checklist FAQ

Before you start digging through drawers.

What if I’m missing a document — should I wait to send everything at once?
No — send what you have as it arrives. Our portal keeps a running checklist per client, and we reconcile against last year’s return and IRS wage transcripts, so we usually spot a missing W-2 or 1099 before you do. Waiting to send a complete package is the single most common cause of returns sliding from March into an extension.
I drive for Uber and have a W-2 job. Which checklist am I?
Both. Your W-2 covers the day job, and the rideshare income files on Schedule C, which means the self-employed list applies: the 1099-K or 1099-NEC from the platform, your mileage log, phone and supply expenses. Mixed filers are the majority of our Tampa clients — the checklist categories stack, they don’t compete.
How far back should my records go?
Bring the current tax year plus your prior year return. Keep supporting records for at least three years after filing (the standard IRS audit window), and seven years for anything involving property, losses, or worthless securities. If we prepare your return, we retain a copy and your depreciation schedules — so switching to Harbor Tax means you stop being the archivist.
Do I really need receipts for every business expense?
You need records, which is broader than paper receipts. Bank and card statements establish that an expense happened; receipts prove what it was. Our rule of thumb: keep receipts for anything over $75, all travel and meals, and every home office and vehicle figure. A clean category summary from QuickBooks with statements behind it survives an audit far better than a shoebox of paper.
When should I get you my documents to avoid an extension?
March 1 is the practical cutoff for a comfortable April 15 filing. Files that are substantially complete by then are e-filed with time to spare. Arrive after April 1 and we’ll likely file a Form 4868 extension — which is free and automatic, but remember it extends filing, not payment. We’ll estimate what you owe so you can pay by April 15 and avoid interest.
Is the first meeting really free, even if I just have checklist questions?
Yes. The first 30 minutes are free for exactly this — we look at your prior return, tell you which checklist applies, what we’d charge, and whether we can save you more than we cost. Roughly one in five people we meet are better off staying with their current setup, and we say so.

Get Started

Your first consultation is free.

30 minutes. No sales pitch. We review your situation and tell you exactly what we can do and what it will cost.

Book a Free Consultation →or call (813) 555-0196
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