1099s for 2026: what changed
The new $2,000 threshold, filing through IRIS, and why most forms are due February 1, 2027.
Tax season 2027
1099s for property managers
The 1099-MISC each owner gets, the 1099-NEC each vendor gets, and the year-end trust books behind both.
Behind before tax season?
The 2027 dates, what an extension does and doesn’t buy you, and what to fix first.
Year-end checklist for property managers
The three-way trust reconciliation, deposits held, advance rent, and the owner statements, in order.
Year-end checklist for contractors
W-9s and 1099s at $2,000, closing out jobs, the equipment you bought, and the two 2026 mileage rates.
Rather hand all this off?
On a free 30-minute call I’ll tell you where your books stand. Getting them current comes with a fixed price in writing.
Getting started
What does a bookkeeper do for a small business?
The day-to-day work explained in plain English, and what you should expect for your money.
Signs your business needs a bookkeeper
The signs it’s time to hand the books off, and what they usually look like.
Bookkeeping vs. accounting for small business
What each one covers, where they overlap, and which one your business needs right now.
How to choose a bookkeeper
The questions worth asking before you hand anyone your books, and the answers you want to hear.
How much does a bookkeeper cost?
What bookkeepers charge for monthly service and cleanup projects in 2026, and how I put a quote together.
Not sure which one applies to you?
Set up a free call. Thirty minutes, I look at your file, and you get a straight answer about what shape it’s in.
Cleanup
Cleanup checklist for QuickBooks Online
The same checklist I work through when a messy QuickBooks file lands on my desk.
Catch-up bookkeeping guide
How to get months or years of books current, one period at a time.
Bank reconciliation for small business
Why reconciling beats every other bookkeeping habit, and how to do it right in QuickBooks Online.
Month-end close checklist
A simple routine for closing each month so year-end stops being a scramble.
Tax-ready bookkeeping checklist
What your CPA actually needs from your books, gathered before they have to ask.
What it costs if I do it instead
Cleanup projects, however far behind the file is, are quoted as one fixed project price, in writing, after I’ve seen the file. The pricing page walks through how I get there.
Rentals, property and trades
Rental property chart of accounts
How to set up QuickBooks Online for rentals so each property shows its own numbers.
Branson short-term rental tax guide
Which Branson taxes the platforms handle, which one you file yourself, and how to track it.
Job costing basics for contractors
How to track cost per job in QuickBooks Online so you know which work actually pays.
Questions
Questions about these guides
Did you write these yourself?
Yes, every one of them. They come out of questions clients actually ask me on the phone, and I write them the way I’d answer on the phone. Nothing here is bought in or spun out of somewhere else.
Do these only apply in Missouri?
Almost all of it applies anywhere in the United States, and I keep books for clients all over the country. The one exception is the Branson short-term rental guide, which covers a local tax you won’t have somewhere else.
Do I need QuickBooks Online to use these?
The checklists work in any system. The step-by-step parts assume QuickBooks Online, because that’s what I work in and what most of my clients use.
Can I just do this myself?
Plenty of people do, and that’s fine by me. Work the checklists and see how far you get. If you hit something that won’t reconcile, or you’re months behind and the pile keeps growing, that’s usually the point to call.
Where should I start?
If your books are current and you’re deciding whether to hand them off, start with what a bookkeeper does and what one costs. If your QuickBooks file is a mess, go to the cleanup checklist. If you’re behind, the catch-up guide.
A Form 990 on extension is due November 16, 2026. Your CPA needs reconciled, fund-level books to finish it, and that’s the part I do.
Filed an extension for 2025? Those returns are due October 15, 2026. Your CPA needs a reconciled 2025 file before then, and the sooner I see it the more room we both have.
1099s for your subs and vendors are due February 1, 2027, and they’re built from a full year of entered payments. If 2026 is behind, the last weeks of the year are the time to catch it up.
1099s for your subs and vendors are due February 1, 2027, the same day your payroll provider sends W-2s. If the 2026 books aren’t entered yet, that’s the first thing I’d fix.
S corporation and partnership returns are due March 15, 2027. Your CPA needs a reconciled 2026 file to file on time.
Individual returns are due April 15, 2027. A reconciled 2026 file is what your CPA needs to file, or to file the extension with real numbers.
Talk to me
Want a second set of eyes on your books?
On a free 30-minute call, you’ll hear plainly what shape your books are in and what I’d recommend. You don’t sign or owe anything unless you decide to go ahead.
A Form 990 on extension is due November 16, 2026. Your CPA needs reconciled, fund-level books to finish it, and that’s the part I do.
Filed an extension for 2025? Those returns are due October 15, 2026. Your CPA needs a reconciled 2025 file before then, and the sooner I see it the more room we both have.
1099s for your subs and vendors are due February 1, 2027, and they’re built from a full year of entered payments. If 2026 is behind, the last weeks of the year are the time to catch it up.
1099s for your subs and vendors are due February 1, 2027, the same day your payroll provider sends W-2s. If the 2026 books aren’t entered yet, that’s the first thing I’d fix.
S corporation and partnership returns are due March 15, 2027. Your CPA needs a reconciled 2026 file to file on time.
Individual returns are due April 15, 2027. A reconciled 2026 file is what your CPA needs to file, or to file the extension with real numbers.
I’ll call you back within 15 to 20 minutes during the day.