Great question and lots of helpful advice here! As someone who's been through several IRS audits as a sole proprietor, I want to emphasize one key point that might get overlooked: the IRS cares most about being able to verify that your expense was legitimate and business-related. Whether you keep a receipt or invoice matters less than making sure the document clearly shows: 1) What you purchased, 2) When you purchased it, 3) How much you paid, 4) Who you paid, and 5) That it was for business purposes. I've found that some invoices are actually better than receipts because they often include more detailed descriptions of services or products. For example, a Stripe invoice might show "Monthly subscription - Business accounting software" while the receipt might just show "Payment to Stripe - $29.99." One practical tip: if you're ever unsure about a particular expense, write a brief note on the back of the receipt/invoice explaining the business purpose. This has saved me multiple times during reviews. The IRS auditor appreciated having that context right there with the documentation. Keep doing what you're doing with tracking everything - that diligence will pay off!

As someone who's been a sole proprietor for about 3 years now, I completely understand this confusion! When I first started, I was saving literally everything - receipts, invoices, email confirmations, you name it. Here's what I've learned through experience and a few conversations with my CPA: the IRS doesn't really care whether it's technically called a "receipt" or "invoice" as long as the document proves you made a legitimate business expense. What matters is that you can show the transaction happened, when it happened, how much it cost, and that it was for your business. For services like Stripe, I usually go with whichever document has more detail. Sometimes their invoices break down fees more clearly than the basic receipt, which can be helpful if you need to categorize different types of charges. One thing that's saved me time is setting up a simple system from day one. I immediately save the document (receipt OR invoice, whichever is more detailed) into a folder on my computer named by month/year. Then at the end of each month, I quickly review everything to make sure I have what I need. The key is consistency - pick one approach and stick with it. You're already on the right track by being diligent about tracking everything!

Another option to consider - I found my S Corp accountant through the Enrolled Agent directory on the NAEA website. Many EAs specialize in small business and S Corps and are much more affordable than larger CPA firms. Plus they're licensed by the IRS and can represent you in case of audit. Most now work virtually so location doesn't matter. Mine is in a different state but handles everything perfectly through secure document sharing. Way better service than I ever got from retail tax chains.

As someone who went through this exact transition last year when my longtime CPA retired, I'd recommend being very cautious with H&R Block for S Corp work. Their retail locations often lack the specialized knowledge needed for proper S Corp tax preparation. I initially tried their Small Business Services (which is separate from their retail offices) and while the preparer was more knowledgeable than the seasonal staff, they still made some concerning errors with my reasonable compensation calculations that I caught during review. What worked for me was using the IRS's "Find a Tax Professional" tool on their website - you can filter specifically for Enrolled Agents and CPAs who work with S Corps. I found three candidates in my price range within a week, all willing to work remotely. The EA I ultimately chose has been fantastic and actually costs less than what H&R Block quoted me. My advice: get quotes from both H&R Block's business division AND a few independent professionals before deciding. Don't let the big name fool you into thinking they're automatically better - often the opposite is true for specialized work like S Corp returns.

You raise an excellent point about participation requirements! Generally, there aren't strict minimum participation thresholds for these types of voluntary employee benefits like dental membership plans. The key is that you offer it to all eligible employees in a non-discriminatory way - you can't pick and choose who gets access based on favoritism. What matters most is having a written policy that clearly defines eligibility (like "all full-time employees" or "employees with 90+ days tenure") and offering it consistently to everyone who meets those criteria. If some employees choose not to participate, that's their decision and doesn't invalidate the business expense deduction for those who do participate. However, you do want to be careful about creating benefit plans that disproportionately favor highly compensated employees or owners. As long as your eligibility criteria are based on legitimate business factors and you're not structuring it in a way that primarily benefits yourself or key executives, you should be fine even with lower participation rates. Document everything - the plan details, eligibility requirements, and communications to employees about the benefit. This shows the IRS that it's a legitimate employee benefit program rather than disguised compensation to select individuals.

I've been through this exact situation with my small marketing agency. The $350 per employee for dental membership plans is absolutely deductible as a business expense under Section 162, and it's actually a smart financial move compared to salary increases. One thing I'd add to the great advice already given - make sure you get a clear breakdown from the dental office about what's included in that $350. Some plans cover preventive care at 100% but only offer discounts on major work, while others might have different structures. This affects how valuable the benefit actually is to your employees and helps justify the business expense. Also, consider asking the dental office if they provide any reporting or documentation specifically for business clients. When I set ours up, they gave me quarterly reports showing utilization rates and savings per employee, which has been helpful for both tax documentation and demonstrating ROI when it comes time to renew. The fact that you're thinking about this proactively shows you care about your employees' wellbeing while being smart about business expenses. That's exactly the kind of ordinary and necessary business expense the IRS expects to see deducted.

Don't overthink this your first year. I did the same thing last year and spent WAY too much time analyzing options. A SEP-IRA is the simplest option to get started with - you can always switch to a Solo 401k next year if your business does well and you want to maximize contributions. For reference, here's what I contributed with around $85k in Schedule C income: - $15,800 to my SEP-IRA (about 20% of my profit after SE tax adjustment) - Still maxed my personal Roth IRA for additional tax diversity The huge advantage of starting with a SEP is you can set it up and fund it until your tax filing deadline including extensions. So you have until October 2026 to actually fund your 2025 SEP contribution if you extend your return.

As someone who just went through this exact decision process, I'd echo what others have said about starting with a SEP-IRA for simplicity. The "3 year rule" you mentioned definitely doesn't exist for SEP-IRAs - that might be something you saw related to defined benefit plans or other tax provisions. One thing I wish someone had told me earlier: don't forget that your SEP contribution is based on your net self-employment earnings AFTER the deduction for half of your self-employment tax. So if your Schedule C shows $50k profit, you'll actually be contributing 25% of something closer to $46k after that adjustment. Also, since you're filing Schedule C, make sure you're setting aside money for quarterly estimated taxes if you haven't already. The retirement contribution will help reduce your tax burden, but you'll still likely owe SE tax on your business income. Good luck with your first year as an entrepreneur!

Has anyone used H&R Block instead of TurboTax for this? I'm wondering if one handles these 409A adjustments better than the other.

I just went through this exact same situation with my RSU sales from last year! The confusion around adjustment codes is so real. What helped me was understanding that the key is avoiding double taxation - since the income from your stock compensation was already reported on your W-2, you need to adjust your basis on the 1099-B to reflect that. For most RSU situations like yours, you'll likely use adjustment code "B" as others mentioned. But here's a tip that saved me a lot of time: before you finalize anything in TurboTax, print out or save a PDF of your tax return and review the Schedule D to make sure your gains/losses look reasonable. If you see huge gains that don't match what you expected, you probably need to double-check your adjustment amounts. Also, if you have any ESPP transactions mixed in with your RSUs, those might need different codes depending on whether they were qualifying or disqualifying dispositions. The supplemental documents that ApolloJackson mentioned are golden for this - definitely hunt those down if you haven't already!