Another approach: check with your startup's law firm. Our company uses Wilson Sonsini, and they offered a reduced rate consultation for employees dealing with 83(b) elections and option exercises. Many of the big firms that work with startups (Cooley, Gunderson, etc.) have programs specifically for startup employees. For QSBS specifically, you need someone who really understands the qualified small business stock exclusion rules. That one's trickier since you're looking 5+ years ahead at potential tax savings, and the requirements are super specific about business types, asset limits, and holding periods.

Don't forget about specialized accountants too! I found my tax person by looking for CPAs who specifically listed "startup equity" or "stock option planning" on their websites. Ended up finding someone who had been handling 83(b) elections for startup employees for 15+ years. Cost was WAY less than an attorney ($250 for an initial consultation, then about $650 to handle the whole 83(b) filing process including all documentation). He also helped me understand the potential QSBS benefits and what records I needed to maintain.

Has anyone found a good way to track these passive losses year to year? I'm using a spreadsheet but it's getting unwieldy with multiple properties.

I've been dealing with this exact same issue in UltraTax for my rental properties! What really helped me understand the distinction was looking at my prior year's Form 8582. The "passive loss carryovers from operating activities" field corresponds to the actual business operations - rent collection, property management, maintenance, repairs, utilities, etc. These are the day-to-day expenses that generate your rental income. The "passive activity carryovers from ordinary business income/loss" field is for the broader business items like depreciation, mortgage interest, and other financing costs that contribute to your overall business loss but aren't directly tied to operations. Since you mentioned you don't materially participate, make sure you're also considering whether you qualify for the $25,000 special allowance if your adjusted gross income is under $100,000. That can sometimes allow you to deduct losses that would otherwise be carried forward. Good luck with your return!

Your situation looks really solid for qualifying under the 2-out-of-5 year rule! Living there continuously from 2016 to March 2023 gives you way more than the required 2 years within your 5-year window before the April 2025 sale. What really strengthens your case is that you've maintained all the hallmarks of primary residence - voter registration, utilities, banking, and mail forwarding all show clear intent that this remains your main home. The fact that you never rented it out is huge because it demonstrates you always intended to return. Your periodic visits back (the 6 weeks, 8 weeks, and 5 weeks you mentioned) actually help document continued use of the property. Even if you weren't physically there every day, the IRS recognizes that temporary work assignments abroad don't disqualify a property from being your primary residence as long as you maintain that intent to return. One practical tip: keep detailed records of your work assignment documentation showing it's temporary, along with all those utility bills and other ties to the property. If you ever get questioned, having that paper trail makes your position bulletproof. You should be in great shape for the capital gains exclusion when you sell!

Based on your situation, you should definitely qualify for the primary residence exclusion! You lived there continuously from 2016 to March 2023, which gives you well over the required 2 years within your 5-year lookback period before your April 2025 sale date. What makes your case particularly strong is that you've maintained all the key indicators of primary residence despite being overseas for work. The IRS looks at the totality of circumstances, and you've got everything lined up perfectly - voter registration, bank statements, utilities, and mail all still tied to the property. Never renting it out is a huge plus since it shows clear intent to return. Your periodic visits (6 weeks in summer 2023, 8 weeks over winter 2023/24, and 5 weeks in May 2024) actually help demonstrate continued use as a residence. The IRS understands that people take temporary work assignments abroad without giving up their primary residence. One thing to keep in mind - make sure you document the temporary nature of your overseas assignment. Keep your employment contract or assignment letter showing it's not permanent. Also maintain that paper trail of all your US connections to the property. If the IRS ever questions your claim, having comprehensive documentation makes your position ironclad. You should be in excellent shape for excluding the capital gains when you sell next April!

I'm dealing with this exact same nightmare right now! Filed my return two weeks ago and got hit with this rejection message yesterday. What's really frustrating is that I actually DID get acknowledgment letters from most of my charities when I made the donations, but they're all in different formats and some don't have the specific language the IRS apparently wants. One thing I discovered is that the acknowledgment needs to include specific elements: the charity's name, date of contribution, location of the contribution, and a description of any non-cash property donated. Some of my letters were missing one or two of these elements, which I think is why my return got flagged. I'm now going back to each organization to request updated acknowledgments with all the required language. It's ridiculous that they changed this requirement in the middle of tax season with basically zero notice. Has anyone found a template or standard language that works for requesting these from charities?

This whole situation is absolutely maddening! I'm a tax preparer and have been dealing with dozens of clients getting hit with these rejections over the past few weeks. What makes it worse is that the IRS issued this new enforcement quietly through their electronic filing system without any formal announcement or guidance update on their website. For anyone still struggling with this, here's what I've learned works best: Contact each charity and specifically request a "donee acknowledgment letter per IRS Publication 526." Most established charities know exactly what this means and can provide the proper format. Make sure the letter includes the charity's legal name (exactly as it appears on their tax-exempt determination), your name, donation date, and a clear description of what you donated. The frustrating part is that many people actually received these acknowledgments when they made their donations but didn't realize they'd need them attached to their tax return. The IRS has always required charities to provide these, but now they're actually checking that taxpayers include them with their filings. It's enforcement of an existing rule, not technically a "new" rule, but the practical effect is the same for all of us scrambling to gather documentation. If you're running out of time before the deadline, definitely consider filing an extension to give yourself more time to collect proper documentation rather than rushing and potentially making errors.

This is such a common confusion for railroad workers! I went through the same thing when I started. The key thing to remember is that railroad employees have a completely different retirement system than regular workers. Think of it this way: regular employees pay into Social Security and Medicare through FICA taxes. Railroad employees pay into the Railroad Retirement system instead through those RRB taxes you're seeing. So when you see "RRB T1 Dis Federal", "RRB Tier 2 federal", and "RRB T1 Med federal" - these are your retirement system contributions, not income tax. Only the "Tax withholding federal" line counts toward your actual federal income tax liability. So in your example, if that federal withholding line totaled $3,000 for the year and you owed $2,500, you'd get back $500 - not the full $4,700 difference from all the withholdings combined. The RRB taxes go toward your railroad retirement benefits, which are generally better than regular Social Security. You'll see these benefits when you retire, but they don't reduce your current year tax bill.

I'm a retired railroad worker who dealt with this confusion for 30+ years! One thing that might help is to think of your paystub as having two completely separate "buckets" of taxes: Bucket 1: Federal Income Tax - This is what goes toward your annual tax return obligation. Only the "Tax withholding federal" amount counts here. Bucket 2: Railroad Retirement System - All those RRB codes (T1 Dis, Tier 2, T1 Med) are like your pension contributions. These never come back as tax refunds because they're not income tax - they're building your future retirement benefits. The Railroad Retirement system is actually pretty generous compared to regular Social Security. Your Tier 1 benefits will be roughly equivalent to what you'd get from Social Security, but Tier 2 is like having an additional pension plan on top of that. Plus, railroad retirement often allows you to retire earlier with full benefits. So don't think of those RRB taxes as "extra" taxes you're paying - think of them as forced savings for a better retirement than most workers get. When you retire, you'll be glad you paid into this system instead of regular Social Security!