I ended up having to call the IRS after getting weird errors on WMR for weeks. Turns out there was a simple issue with my return they needed to verify. after spending like 3hrs on hold I finally got someone who fixed it in 5 minutes. if the error continues maybe try calling

I've been having similar issues with the Where's My Refund tool lately! Filed about a month ago and it's been giving me random errors like this too. From what I've learned, it's usually just system maintenance or temporary glitches - especially if you're checking during weird hours like 5am. The IRS systems are pretty outdated and can be unreliable. I'd recommend trying again later today during normal business hours (like 10am-4pm) and see if it works better. If you keep getting errors for more than a couple days, then it might be worth looking into your transcript or calling them directly. But most likely it's just a temporary system hiccup!

Has anyone had experience with the deferred salary situation specifically? I had something similar happen where I took stock instead of salary, and when the company went under, the IRS initially questioned my write-off. I had to fight to prove it wasn't just a capital loss.

One thing to keep in mind with your angel investment is that you might also want to look into whether it qualifies as Qualified Small Business Stock (QSBS) under Section 1202. Even though the investment became worthless, if it was QSBS when you acquired it, you could potentially get better tax treatment on any gains from other QSBS investments by increasing your exclusion amount. Also, regarding your $22,000 in unrealized stock losses - if you're planning to hold onto those stocks long-term, consider whether tax-loss harvesting makes sense. You could sell the losing positions before year-end to realize the losses, then use them to offset any capital gains plus up to $3,000 against ordinary income. Just be careful about the wash-sale rule if you want to buy back similar positions within 30 days. The timing advice from Amara is spot-on. Since you're already planning to work with a CPA, make sure to gather all your documentation now - startup dissolution papers, final investor communications, employment agreements showing the salary deferral arrangement, etc. Having everything organized will make your CPA consultation much more productive and potentially save you money on their fees.

Has anyone considered that maybe an LLC with S-Corp election could help with the self-employment tax issue? If the Airbnb activity is definitely a business and not just rental income, you could potentially save on SE tax by taking a reasonable salary and the rest as distributions.

This is such a common confusion! I went through the same thing when I started hosting. The key thing to understand is that the IRS uses a "facts and circumstances" test to determine if your Airbnb income is subject to self-employment tax. From what you've described about your sister's situation, she's likely crossing into self-employment territory. The combination of personal cleaning, welcome baskets, providing utilities, and active management suggests she's providing "substantial services" beyond just renting space. Here's what I learned matters most: if the average guest stay is 7 days or less AND you're providing services primarily for the guest's convenience (rather than just maintaining the property), it's usually considered a business activity subject to SE tax. The welcome baskets might seem small, but they're actually a red flag to the IRS because they show you're going beyond basic property rental into hospitality services. Combined with her doing all the cleaning personally, it really looks like active business income rather than passive rental income. My advice? Have your sister track everything carefully - guest stay lengths, time spent on management activities, and all the services she provides. This documentation will be crucial whether she ends up owing SE tax or if she ever gets audited.

Great discussion here! I want to emphasize something that's been touched on but bears repeating - the timing of your 83(b) election was crucial. Since you filed it in 2016 when the FMV was zero, you've effectively locked in your basis at $0 and converted what would have been ordinary income at vesting into long-term capital gains treatment. One thing to keep in mind: make sure you have documentation of your 83(b) election filing. The IRS doesn't send acknowledgments, so you'll want proof that it was filed timely (within 30 days of grant) in case there are any questions during audit. A certified mail receipt or other delivery confirmation is your best friend here. Also, when the sale happens, double-check that your company's tax reporting aligns with your 83(b) election. Sometimes there can be discrepancies in how the company reports vs. what your actual tax treatment should be based on your election.

One additional consideration that hasn't been mentioned yet - if your LLC units are subject to vesting and the company hasn't sold yet, make sure you understand what happens if you leave the company before the liquidity event. Many LLC operating agreements have "bad leaver" provisions that could affect your tax treatment or even result in forfeiture of unvested units. Also, since you mentioned the units only vest upon sale or IPO, you'll want to confirm whether there are any interim valuation events that could trigger partial vesting or affect your basis calculation. Some agreements have provisions for secondary sales or tender offers that could complicate the tax picture. The 83(b) election protects you from ordinary income treatment at vesting, but it doesn't necessarily protect against forfeiture provisions in your grant agreement. Worth reviewing those terms with both a tax professional and potentially an employment attorney if there are significant amounts at stake.

This is such a helpful thread! I'm dealing with a similar situation but with a twist - my rental condo has a 99-year land lease AND I'm planning some major renovations (new flooring, updated kitchen, bathroom remodel). Based on what everyone's shared, I'm feeling confident about allocating 95-100% of my original purchase price to the building for depreciation purposes. But I'm wondering about the timing of my renovations - should I wait until after I establish my initial depreciation schedule, or does it not matter? Also, for those capital improvements mentioned by @Emma Olsen, do I need to depreciate them over the same 27.5-year period as the building, or do different improvements have different recovery periods? I'm particularly curious about flooring vs. kitchen appliances vs. bathroom fixtures. Thanks for all the great advice in this thread - it's exactly what I needed to hear!

This is such a valuable discussion! I'm a CPA who specializes in rental property taxation, and I wanted to add a few important considerations that haven't been fully addressed yet. First, regarding the 95-100% building allocation for leasehold condos - this is generally correct, but you should also consider the remaining term of the lease. With a 99-year lease that's relatively new, the leasehold interest has substantial value. However, if this were a lease with only 10-15 years remaining, the allocation might be different. Second, I'd strongly recommend getting a professional appraisal that specifically addresses the land/building allocation in your leasehold situation. While it costs around $400-600, it provides solid documentation that the IRS will respect if questioned. Many of my clients have found this small investment pays for itself quickly through increased depreciation deductions. Finally, make sure you understand the implications when you eventually sell the property. All that depreciation you're claiming will be subject to depreciation recapture at a maximum rate of 25%, so factor that into your long-term tax planning. The advice about documenting your reasoning and keeping the lease agreement on file is spot-on. I've never seen the IRS challenge a well-documented leasehold depreciation allocation that's based on sound reasoning.