Don't overthink this! I'm in exactly the same situation (S-Corp owner who took a W-2 job). The simplest approach is just to pay yourself a reasonable bonus at year-end from the S-Corp based on the actual work you do for it. This allows you to make both employee and employer contributions to your solo 401(k). Remember that your total employee contributions across ALL 401(k) plans can't exceed the annual limit ($23,000 for 2025 if under 50), but each business can make separate employer contributions.

This is exactly the kind of situation where having both income streams can actually work in your favor! Since your W-2 job covers living expenses, you have more flexibility in how you structure your S-Corp compensation. One approach that's worked well for me in similar situations is to focus on maximizing the employer contribution from your S-Corp rather than trying to split employee contributions between both plans. You can contribute up to 25% of your S-Corp compensation as an employer contribution, which could be quite substantial depending on your business income. For the compensation piece, consider what you'd actually pay someone else to maintain your S-Corp at its current level. Even if you're spending less time on it now, if it's still generating significant revenue, there's real value in the oversight and strategic decisions you're making. Document the specific activities you perform and their market value. Also worth noting - if your S-Corp has been consistently profitable, you might want to consider whether converting to a traditional LLC makes sense now that it's no longer your primary income source. The S-Corp election made sense when you were maximizing retirement contributions, but depending on your current situation, the additional administrative burden might not be worth it anymore. Have you run the numbers on what your total tax savings would be comparing different compensation structures?

Has anyone considered the advertising expense angle? While club dues aren't deductible, advertising expenses definitely are. If you're using the photos taken at the country club as part of your advertising materials, couldn't you argue that a portion of the dues represents the cost of creating advertising content?

I've been following this discussion closely as I'm dealing with a similar situation with my photography business. One thing that hasn't been mentioned yet is the potential for creating a legitimate rental agreement with the country club for specific business use. Instead of trying to deduct membership dues, you could approach the club about paying a separate hourly or daily rate specifically for commercial photography access during off-peak hours. Many clubs are actually open to this because it generates additional revenue without interfering with member play. This creates a clear business expense that's completely separate from any personal membership benefits. I've done this with several venues and it's much cleaner from a tax perspective - you're paying specifically for business use of the facility, not for membership privileges that could be used personally. The key is making sure the arrangement is documented properly and the payments are separate from any membership fees. This way you avoid the Section 274 restrictions entirely since you're not deducting club dues - you're deducting legitimate business facility rental costs.

Former brokerage employee here. Another factor nobody mentioned yet: CORRECTIONS. Investment companies receive corrected information from issuers all the time. If they rushed forms out early, they'd end up sending corrected 1099s to like 30-40% of clients, which would mean you'd have to amend your return. By waiting until most corrections are processed (typically early-mid February), they reduce the number of corrected forms to around 5-10%. It's actually better for most customers even though it feels annoying when you're waiting.

Anyone know if this is the same for cryptocurrency tax forms? I'm using coinbase this year and wondering when those will be ready.

Doesn't this all depend on how the original tax return was filed? Did you actually report the home sale on the 2023 return in the first place? If not, that might be why the IRS is questioning it. When I sold my primary residence, I reported it on Form 8949 with code "H" to show it was my primary residence and excluded under Section 121, then carried that to Schedule D. If you just didn't report the sale at all (thinking you didn't need to because of the exclusion), that might be your problem.

That's exactly the issue! When you qualify for the Section 121 primary residence exclusion, you still need to report the sale on your tax return - you just apply the exclusion to reduce or eliminate the taxable gain. The IRS computer systems match up the 1099-S they receive from the closing company with what's reported on your return. When they don't see the sale reported at all, they assume you forgot to include it and send those scary letters. The fix is straightforward but requires filing Form 1040X (amended return). You'll report the sale on Form 8949 and Schedule D, calculate your gain (sale price minus your adjusted basis including improvements), then apply the $250,000 exclusion. Since your gain was around $355,000 ($510k - $155k), you'll still have about $105,000 of taxable gain after the exclusion, but that's much better than being taxed on the full $355,000! Don't panic - this is a very common mistake and the IRS sees it all the time. Just make sure to include good documentation of your mom's ownership and residence history when you file the amendment.

Anyone know if there's a way to opt out of the IP PIN program once you've opted in? I initially signed up after some concerns about identity theft, but now it feels like an extra hassle every year.

Just to add some clarity on the timing - I've been in the IP PIN program for 3 years now and the pattern is pretty consistent. New IP PINs are typically available online through your IRS account starting around December 28th-January 2nd. The physical CP01A notices usually arrive in the mail between January 10th-20th, depending on your location. I'd definitely recommend setting up your IRS online account if you haven't already - it's much more reliable than waiting for mail, especially if you're planning to file early. You can access it through the "Get an IP PIN" tool on IRS.gov once the new year hits. Just make sure you have all your previous year tax info handy for identity verification when you log in. Pro tip: Set a calendar reminder for early January to check your online account. That way you can get your PIN and file as soon as W-2s and other documents are ready!