Answer:

Usually no—a home office deduction generally requires a trade or business. Most rental activity reported on Schedule Eis treated as an investment activity, so the home office rules typically don’t apply. The answer can change if your rental activity rises to the level of a trade/business (or you qualify as a real estate professional and materially participate).

What makes it “yes” instead of “no”:

• You provide substantial services (more like a hotel/short-term rental operation)

• The activity is structured/operated as a business with real operational intensity

• You meet real estate professional requirements and material participation (facts matter)

If you think it might qualify, here’s what I’ll ask for:

• Property count + average hours per month spent managing them

• Short-term vs long-term rental mix

• Services provided (cleaning, concierge, breakfast, etc.)

• Whether you have other W-2 / businesses competing for time

If you want the clean answer without guessing, book a quick call and we’ll decide whether this is a real deduction or an audit story.

Answer:

Yes, an S-corp owner can usually deduct health insurance—but it has to be set up correctly. In most cases, the policy must be treated as company-paid and included on the shareholder’s W-2 (Box 1 wages, not subject to Social Security/Medicare if structured properly). If it’s run wrong, you lose the clean deduction.

Quick checklist (what we want to see):

• Policy is in the shareholder’s name or the S-corp pays/reimburses under a formal plan

• Premiums are paid by the company (or reimbursed) and properly recorded

• Amount shows on W-2 Box 1 as S-corp health insurance

• You have earned income to support the deduction on the personal side

Common “this breaks it” issues:

• Paying personally with no reimbursement trail

• Trying to deduct it on Schedule A or as an unreconciled expense

• Multi-owner S-corps with no consistent plan

If you’re an S-corp and paying health insurance, this is one of those “do it right or don’t do it” items. We’ll make it clean.

Answer:
A Roth conversion is taxable unless you have after-tax basis in traditional IRAs. Form 8606 tracks that basis. If you don’t document basis, the IRS assumes it’s $0, and your conversion becomes fully taxable even if you already paid tax on prior contributions.

What we need from you:

• Prior-year Form 8606 (if any)

• Year-end balances of all traditional/SEP/SIMPLE IRAs

• 1099-R for the conversion

• Any record of non-deductible contributions (and years)

The gotcha people miss: the pro-rata rule
Even if you converted only “the after-tax part,” the IRS looks at all IRA balances together for the calculation.

If you’re converting and you’re not 100% sure about basis, don’t guess. That’s how people donate money to the IRS for no reason.

Answer:

Penalty relief is possible, but it’s not magic. Abatement is most successful when you can show reasonable cause, a good compliance history, and a fast correction once the issue was discovered. A good letter is factual, specific, and documented—no melodrama.

What helps your case:

• First-time issue / otherwise compliant history

• Clear reason (move, illness, incorrect notice, administrative error, etc.)

• Proof you corrected quickly (payment plan, filed return, etc.)

What hurts your case:

• Repeated late filing/payment

• No documentation

• “I forgot” (not a strategy)

If you have a penalty notice, send it over and we’ll tell you if it’s worth fighting—or if you’re better off paying and moving on.

Redwood Tax is based in Rochester (1100 University Ave Suite 117) and works with clients across New York State, including New York City and WNY. Most work is handled securely and efficiently through remote document collection, structured checklists, and proactive planning—without the “please bring a shoebox of receipts” energy.

Who we’re a fit for (NYC + WNY):

• W-2 + equity comp + multi-state complexity

• S-corp owners and contractors

• Real estate investors (multi-property, multi-entity)

• People who want planning, not surprises

What remote engagement looks like:

• Secure upload + organizer

• Clean list of open questions (no 37-email chains)

• Delivery with action items and tax-year planning

NYC or WNY, same rules: clean books, correct filings, no drama. Book a call.