Sole prop, single-member LLC, partnership, or S-corp — your business return and your personal return usually aren't two separate problems, they're one. I help small business owners plan ahead, not just file after the fact, so April never brings a surprise.
A good small business tax relationship runs year-round, not just at filing time. Here's what that typically includes.
Sole prop, LLC, S-corp, or partnership — the right structure changes your tax bill, your liability exposure, and your paperwork. Best decided before you incorporate, not after.
Calculated and tracked through the year so you're never blindsided by what you owe, and never hit with an underpayment penalty for guessing wrong.
For most small businesses, your business income flows directly into your personal return. Preparing them together — not separately — is how errors get caught before they're filed.
Decisions made in October affect what you owe in April. Regular check-ins mean nothing gets locked in without understanding the tax impact first.
Electing S-corp status can reduce self-employment tax once profit is high enough — but the payroll and filing requirements that come with it aren't worth it for everyone.
Bookkeeping isn't included in advisory work, but clean books make everything else faster and more accurate — happy to coordinate with your bookkeeper or recommend one.
A lot of hosts start out thinking of it as extra cash on the side, on top of a full-time job or another business. Tax-wise, it's its own animal, and it's easy to get wrong without realizing it.
A typical long-term rental is passive income. Once the average guest stay drops to about 7 days or less — the norm for most Airbnbs — the IRS generally treats it as a business activity instead. Add hotel-like services (daily cleaning, breakfast, concierge-style help) and it can trigger self-employment tax on top of that.
The structure itself (not the land under it) can be depreciated, lowering your taxable income each year. A cost segregation study can break the property into components with shorter depreciable lives, front-loading a much bigger deduction into the early years — worth exploring once the numbers are meaningful.
Basis is the number behind both your depreciation deductions and your eventual gain on sale. Every dollar of depreciation claimed lowers that basis — which usually means part of any gain gets taxed back later at a less favorable rate (depreciation recapture).
If average stays run 7 days or less and you materially participate in running it, losses aren't limited the way an ordinary rental's would be — they can potentially offset W-2 or other income. Get the details wrong, though, and the IRS can disallow the loss entirely.
I've owned and run a business abroad since 2018. I know what it's like to make a structuring decision without fully understanding the tax consequence until later. I don't just hand you a number and let you deal with the reaction — I walk you through why it is what it is, and I look for ways to bring it down before the year ends, not after.
It depends on your profit level, state, and long-term plans. S-corp status can reduce self-employment tax once net income is high enough to justify the added payroll and filing requirements, but it isn't automatically the right move for every business — this is exactly what an entity structuring consultation is for.
If you expect to owe $1,000 or more for the year and don't have enough withheld from other income, the IRS generally expects quarterly estimated payments. Missing them can trigger an underpayment penalty even if you pay everything in full by the filing deadline.
For sole proprietors, single-member LLCs, and most pass-through entities, yes — business profit flows through to your personal Form 1040 via Schedule C or a K-1. That's why business and personal returns are usually most accurate when prepared together rather than treated as two separate problems.
It depends on the average length of stay and how involved you are. Most Airbnbs, where the average stay is 7 days or less, are treated as a trade or business rather than passive rental activity — which changes how any losses are treated, and can trigger self-employment tax if you're also providing hotel-like services such as daily cleaning or breakfast.
Yes — the building itself (not the land) can be depreciated, and a cost segregation study can accelerate a meaningful portion of that deduction into the first few years instead of spreading it over decades. Keep in mind depreciation lowers your basis, which affects the tax bill when you eventually sell.
Bookkeeping isn't included in tax preparation or advisory services — keeping it separate keeps the focus on planning and strategy, where a CPA adds the most value. A trusted bookkeeper referral is available on request.
A sole prop or single-member LLC return starts at $750; S-corps, partnerships, and multi-member LLCs start at $1,200. Ongoing advisory packages with quarterly planning start at $1,450/year. See the full pricing page, or take the quiz for a ballpark specific to your situation.
A short conversation about your business is the place to start — I'll tell you honestly whether a quick annual filing or ongoing planning makes more sense for where you are.