I have an S corp making about $200k/year while I work full-time elsewhere. My accountant made me set up payroll and take a $60k salary even though I argued I barely spend time on it. His reasoning: if your business makes good money, the IRS assumes you're providing valuable services. Think about it this way - if your business is successful enough to make $400-650k, someone's expertise is driving that success. If it's yours, you need to be compensated with a reasonable salary. The reasonable salary doesn't mean you have to take all profits as salary - just what would be reasonable for the services you provide. The rest can still be distributions.

I went through this exact situation two years ago and learned the hard way that the IRS doesn't care about your other employment when it comes to S corp salary requirements. I was making $120k at my day job and my S corp was pulling in about $300k, but I wasn't paying myself any salary from the business. Got audited and the IRS agent was very clear: if your S corp is generating substantial profit and you're providing services (even part-time), you need reasonable compensation. They don't look at your total income across all sources - they look at each entity separately. I ended up having to pay back payroll taxes plus penalties. My advice: once your S corp is consistently profitable (especially at the levels you're talking about), set up payroll immediately. The "reasonable" salary depends on your industry and role, but for a business making $400-650k, you're definitely looking at a significant salary requirement. The Medicare taxes alone make it worth getting this right from the start. Don't make the same mistake I did - the penalties and interest add up fast.

I had this exact same issue a few weeks ago! Super frustrating when you need your transcript urgently. What worked for me was actually a combination of things - first I cleared all my browser data (cookies, cache, everything), then I tried accessing the site at like 6 AM when their servers aren't as loaded. When I still got the authorization error, I ended up going through the full ID verification process again which was annoying but only took about 15 minutes. The key is having all your documents ready beforehand - SSN, last year's AGI, a credit card or bank account number for verification, and your phone for the text code. Once I got back in, I made sure to bookmark the direct transcript page and log in monthly now so it doesn't happen again. Good luck with your mortgage application!

This happened to me too about a month ago! Super annoying timing since I was also dealing with a mortgage application. What finally worked for me was using incognito/private browsing mode after clearing all my cookies. Sometimes the IRS site gets confused with old session data. If that doesn't work, the verification process isn't too bad - just make sure you have your AGI from last year's return handy since that's usually what trips people up. The whole thing took me maybe 20 minutes once I had everything ready. Hope you get it sorted quickly for your mortgage app!

For a super simple return with just an HSA, I've been using H&R Block's free online version for years. They still include HSA Form 8889 in their free tier unlike TurboTax. Their interface isn't as slick but it gets the job done without the surprise fees.

I went through this exact same frustration last year! TurboTax definitely changed their policy on HSAs - it used to be included in the free version. The $120 total cost is outrageous for such a simple return. I ended up switching to FreeTaxUSA and it's been great. HSAs are handled completely free on the federal return, and state filing is only $15. The interface isn't as flashy as TurboTax but it walks you through everything clearly. I've used it for two years now with my HSA and haven't had any issues. The IRS Free File program is also worth checking if your AGI is under $73K - several participating companies offer completely free filing including HSA support. Don't let TurboTax's marketing fool you into thinking you need their overpriced service for something this basic!

From personal experience with our family's C corp, you should also consider whether the buyout affects your company's S corporation eligibility for the future, if that's something you might want to pursue. After our shareholder redemption, we realized we finally had the right ownership structure to elect S status and save on taxes.

One thing I haven't seen mentioned yet is the importance of getting a proper business valuation if you haven't already. The IRS can challenge the purchase price in an audit if it seems unreasonable compared to fair market value, especially in closely-held C corporations where arm's length transactions are rare. We learned this the hard way when our initial buyout price was based on book value rather than fair market value. The IRS questioned whether part of the "purchase price" was actually disguised compensation to the departing shareholder, which would have changed the tax treatment completely. We ended up getting a formal appraisal from a certified business appraiser after the fact to support our position. Also, make sure your corporate minutes clearly document the business purpose for the buyout - resolving shareholder disputes, eliminating management conflicts, etc. The IRS looks for legitimate business reasons beyond just wanting to change ownership percentages. Keep detailed records of the meetings where the decision was made and the rationale discussed.

Diego, you're absolutely right to question this! The double taxation concern is totally valid, but the good news is you can avoid it with proper planning. First, check if you qualify for Traditional IRA deductions based on your income and workplace retirement plan status. If you do qualify, claiming those deductions on your tax return will essentially "undo" the initial taxation on that money. If you don't qualify for deductions due to income limits, you're making non-deductible contributions and should file Form 8606 each year to track your "basis" (money already taxed). This protects you so that when you withdraw in retirement, you only pay tax on the growth, not the contributions you already paid tax on. One alternative to consider: if you're above the income limits for Traditional IRA deductions, you might want to look into a Roth IRA instead (if eligible) or a backdoor Roth conversion strategy. With Roth, you pay taxes upfront but withdrawals in retirement are completely tax-free. The key principle: you should never pay tax twice on the same dollar. Either you get the deduction now and pay tax later (Traditional), or you pay tax now and never again (Roth). Make sure you're taking advantage of whichever strategy fits your situation!

Diego, you've stumbled onto one of the most confusing aspects of retirement planning, but don't worry - you're NOT getting double-taxed if you handle this correctly! The confusion comes from thinking that all Traditional IRA contributions are "after-tax" just because the money came from your bank account. But here's the key: Traditional IRA contributions are usually TAX-DEDUCTIBLE, which means you get to subtract them from your taxable income when you file your return. So here's what should happen: You contribute money from your checking account → You claim the Traditional IRA deduction on your tax return → This reduces your taxable income and essentially gives you back the taxes you already paid on that money → When you withdraw in retirement, you pay taxes then (but only once, not twice). However, there are income limits for these deductions. If you make too much money or have certain workplace retirement plans, you might not qualify for the full deduction. In that case, you'd file Form 8606 to track your "basis" (money already taxed) so you don't get taxed again on those contributions when you withdraw. Check your eligibility for the deduction first - most people qualify and can avoid the double taxation entirely. If you've been missing these deductions on past returns, you can file amended returns to claim them. You haven't messed up your retirement planning, you just need to make sure you're taking advantage of the tax benefits available to you!