One thing I wish I had known earlier - make sure you're tracking your time spent on your Poshmark business! The IRS uses this to determine if you qualify as a business vs. hobby. If they classify it as a hobby, you can't deduct expenses that exceed your income. Keep a simple log of hours spent sourcing, photographing, listing, packaging, and shipping. This documentation helps establish that you're running a legitimate business with profit motive, not just casually selling items. The "hobby loss rule" can be a real problem for resellers if you have a loss year or the IRS decides to audit. Also, since you mentioned setting up better tracking for this year - consider opening a separate business checking account even if you're not formally incorporated. It makes record-keeping so much cleaner and shows the IRS you're treating this as a real business operation.

Great question about record keeping! A simple spreadsheet is absolutely sufficient for tracking your business hours - you don't need fancy apps or minute-by-minute precision. I track mine in 15-30 minute blocks which works well for IRS purposes. For your time log, include columns for: Date, Activity (sourcing, listing, shipping, etc.), Start/End times, and total hours. The IRS mainly wants to see that you're spending substantial and regular time on the business, showing profit motive rather than casual hobby activity. Regarding the separate business checking account that QuantumQuasar mentioned - this is excellent advice even for sole proprietors. Most banks offer simple business checking accounts, and it makes your Schedule C preparation so much easier when all business income and expenses flow through one dedicated account. It also strengthens your position if the IRS ever questions whether you're operating a legitimate business. One more tip: since you're already organizing last year's receipts, consider scanning them or taking photos as backups. Physical receipts can fade or get damaged, and having digital copies stored securely gives you extra protection for potential audits.

I've been dealing with a similar situation in my S Corp. One thing I'd add to the excellent advice here is to make sure you're consistent with how you handle these premiums throughout the year, not just at year-end. We set up our payroll system to add the health insurance premiums to our W-2 wages each pay period (subject to income tax but not FICA), rather than waiting until December to make one big adjustment. This gives a more accurate picture of our actual compensation throughout the year and avoids any potential issues with quarterly estimated tax payments. Also, regarding the equity concern with your partner - we addressed this by having our attorney draft language in our shareholder agreement that specifically states how health benefits are handled. It clarifies that the company provides health insurance coverage to all shareholders regardless of premium cost, which removes any ambiguity about one partner subsidizing the other's coverage. This protects both partners if ownership changes in the future.

One important consideration that hasn't been mentioned yet is the timing of when you establish your health insurance policy through the S Corp. The IRS requires that the health insurance plan be "established under" the business for shareholders to qualify for the self-employed health insurance deduction. This means if you currently have individual policies that you're personally paying for, you can't simply have the S Corp reimburse you and get the tax benefits. The corporation needs to either be the policyholder or have a formal arrangement where it pays the premiums directly to the insurance company. Also, make sure you're not mixing this benefit with any health savings account (HSA) contributions if you have high-deductible health plans. The tax treatment can get complicated when you combine S Corp health insurance benefits with HSA contributions, so you'll want to coordinate these carefully to maximize your tax advantages. The unequal premium amounts between you and your partner really isn't uncommon - family vs. individual coverage naturally creates different costs, and the IRS doesn't expect or require equal dollar benefits for equal ownership percentages.

One important thing nobody's mentioned yet - be careful how you document the "fair market value" of collectibles. The IRS is VERY picky about this and it's a common audit trigger. FMV isn't what you paid, what it's insured for, or what similar items sell for at specialty shops. It's specifically what a willing buyer would pay a willing seller when neither is under pressure. For action figures, I'd recommend looking at actual completed eBay sales (not just listings) of the same items in similar condition. Screenshot these as evidence. And be conservative in your valuations - better to undervalue slightly than to raise red flags.

Just wanted to add another perspective on the appraisal requirement - I went through this exact situation last year with my vintage baseball card collection. One thing that helped me was finding an appraiser who specializes in collectibles and offers "batch pricing" for large collections. Instead of charging per item, they charged a flat fee based on the total estimated value range. This made it much more affordable than I initially thought. Also, keep in mind that the appraisal fee itself can be deductible as a miscellaneous expense related to tax preparation. So while you're paying upfront, you do get some of that back. The documentation requirements are strict, but if you're organized about it (taking photos, keeping receipts, noting condition), the whole process is manageable. And honestly, having that professional appraisal gives you peace of mind that your valuation will hold up if the IRS ever questions it. The splitting across tax years strategy mentioned earlier is legitimate, but just make sure you're genuinely spreading out the physical donations too - not just artificially timing the paperwork.

18 Random but related tip - if you're fronting expenses and getting reimbursed later, use a good rewards credit card! I put about $9k of company expenses on my card last year and earned enough points for a round-trip flight. Company gets their supplies, I get reimbursed fully, AND I get travel rewards. Triple win!

Great question! You're absolutely right to be organized with your documentation - that's key. Since you're getting fully reimbursed through your company's expense report system, you don't need to report these transactions on your personal tax return at all. This falls under what the IRS calls an "accountable plan" since you're providing receipts, documenting business purposes, and getting reimbursed for actual expenses. The company treats these as their business expenses, and from your perspective, it's like they paid the vendors directly - you were just the middleman. The fact that you temporarily used your personal credit card doesn't change the tax treatment. No need to report the $4-5k in purchases as deductions, and the reimbursements aren't considered income to you. Keep doing what you're doing with the documentation though - those records are important if you ever need to prove the business connection of the expenses.

Based on my experience and what I've seen others go through, the timeline really varies but here's what you can expect: Most people see their refunds 2-4 weeks after successful ID verification through ID.me. Since you just verified last week, you're still well within the normal timeframe. A few tips while you wait: - Check your IRS account transcript online if you haven't already - it often updates before WMR does - Don't panic if you see codes 570/971 on your transcript right after verification - that's normal - If you claimed EITC or Child Tax Credit, it may take longer due to PATH Act holds The good news is that once you've successfully verified through ID.me, that step is completely done. Now it's just a matter of normal processing time. Hang in there!

I went through identity verification about 3 weeks ago and just got my refund yesterday! Here's what my timeline looked like: verified through ID.me on February 14th, transcript updated with codes 570/971 about a week later, then got the 846 code (refund issued) this past Monday. The refund hit my bank account Wednesday morning. One thing that helped my anxiety was setting up informed delivery with USPS and checking my transcript weekly instead of daily. The WMR tool never updated for me until literally the day before I got my money, so don't rely on that too heavily. You're still early in the process since you just verified last week, so try not to stress too much yet!