This is a great question that highlights how complex RSU taxation can be! As someone who's navigated similar confusion, I think the key insight from the discussion so far is that wash sale rules only apply to losses, not gains. But here's another angle to consider - even if your sale was at a loss, RSU vests can sometimes avoid triggering wash sales due to the "compensation vs. purchase" distinction that Sean mentioned. The IRS has generally treated RSU vests as compensation events rather than voluntary stock purchases. That said, I've noticed some brokerages are becoming more conservative in their wash sale reporting, especially with company stock transactions. They might flag potential wash sales even in borderline cases to avoid underreporting issues. For future reference, it's worth tracking not just the timing but also the exact share lots and cost basis of your RSU sales versus vests. Sometimes what looks like a wash sale on the surface doesn't actually meet all the technical requirements when you dig into the details.

Great question about fractional shares and brokerage differences! In my experience, the wash sale rule applies based on the number of shares involved, not necessarily requiring exact quantity matches. If you sold 50 shares at a loss and then vest 100 shares within 30 days, the wash sale would typically apply to 50 shares (the lesser amount). For fractional shares specifically, most brokerages will round to determine wash sale applicability, but the exact methodology can vary. Some use a "substantially all" standard where small fractional differences don't prevent wash sale treatment. Regarding brokerage differences - absolutely! I've seen significant variations in how different platforms handle RSU wash sale reporting. Fidelity tends to be more conservative and flags borderline cases, while E*Trade (now Morgan Stanley) sometimes misses cross-account wash sales entirely. Schwab falls somewhere in the middle. My recommendation is definitely to do your own calculations and not rely solely on 1099-B reporting. I keep a spreadsheet tracking all my company stock transactions with dates, quantities, and cost basis. When tax time comes, I compare my analysis to what the brokerage reports and make adjustments on my return if needed. The IRS ultimately cares about the correct tax treatment, not what your brokerage happened to report.

Does anyone know if there are different rules depending on when someone inherited an IRA? My aunt left me one back in 2019 and I was told different rules applied then.

One important thing to consider that hasn't been mentioned yet is state tax implications. While everyone's focused on federal taxes (which are definitely the main concern), some states have their own rules for inherited IRA distributions. For example, some states don't tax retirement account distributions at all, while others might have different timing rules or exemptions for inherited accounts. Since you're dealing with a $67k inheritance, the state tax piece could be significant depending on where you live. Also, make sure you're working with the IRA custodian to properly retitle the account as an inherited IRA. This needs to be done correctly to preserve the tax-deferred status and avoid any immediate tax consequences. The custodian should be familiar with the process, but it's worth double-checking that they're following the proper procedures. Good luck with everything, and sorry for your loss. Inheriting retirement accounts is never easy, both emotionally and from a tax planning perspective.

Does anyone know if those donation value calculators online are actually accurate? Like when it says a used men's shirt is worth $5-7 for tax purposes? I always worry I'm either claiming too little or too much.

As someone who's been through this exact situation, I can tell you that unfortunately without proper documentation for a $1200+ donation, you're in a tough spot. The IRS is pretty strict about the written acknowledgment requirement for donations over $250. However, here's what you might still be able to do: Try to identify which veterans organization owned that donation bin. Many of these bins have small labels or contact information somewhere on them. You could drive back to the location and check, or call the grocery store to ask if they know which charity uses that bin. If you can identify the organization, contact them directly and explain your situation. Some charities will work with you to provide retroactive documentation if you can provide details about when and where you made the donation. It's not guaranteed, but worth trying. For future reference, I always take a photo of the donation bin (showing the charity name) and photos of what I'm donating before I drop it off. This creates a paper trail that makes getting documentation much easier later. The good news is that even if you can't claim this year's donation, you'll be better prepared for next time!

Just a heads up - don't forget to consider state filing requirements too! Depending on your state, you might need to file additional self-employment forms at the state level. I learned this the hard way last year 😭

I'm in almost the exact same boat - W-2 from my day job plus a 1099-NEC from some freelance work I picked up. After reading through all these responses, I'm definitely leaning toward checking out FreeTaxUSA instead of paying the premium for TurboTax Self-Employed. One thing I'd add is to make sure you track any business expenses related to your 1099 work - things like equipment, supplies, mileage, or even a portion of your internet bill if you worked from home. These can really help offset the self-employment tax burden. I wish I had been better about tracking expenses throughout the year instead of scrambling to remember everything now at filing time. Thanks everyone for sharing your experiences - this thread has been super helpful!

As someone who's dealt with questionable tax situations before, I want to echo what everyone else has said - this is absolutely a red flag situation you should avoid. I had a similar experience a few years ago with a company that claimed their employees were "independent contractors" who didn't need to worry about tax withholdings. Long story short, I ended up owing thousands in back taxes and penalties when the IRS caught up with the situation. Even though I was just following what my "employer" told me, I was still personally liable for all the unpaid taxes. The key thing to remember is that the IRS holds YOU responsible for reporting your income correctly, regardless of what anyone else tells you about special arrangements or loopholes. If it sounds too good to be true (like not having to pay income taxes on money you earn), it probably is. You're making the right choice by walking away from this opportunity. There are plenty of legitimate outdoor education programs out there that operate above board and won't put you at risk of serious tax trouble down the road.

I completely agree with everyone here - this is definitely a situation to avoid. I've seen several cases where people got involved with PMAs thinking they were legitimate tax strategies, only to face serious consequences later. What's particularly concerning about your situation is the combination of red flags: the "donation-based" payment system, claims that employees don't need to file taxes, and the vague explanations about the organizational structure. These are classic hallmarks of abusive tax schemes that the IRS actively pursues. Even if the director genuinely believes this arrangement is legal, that won't protect you if the IRS determines otherwise. I've seen cases where well-meaning business owners convinced themselves they'd found a legitimate loophole, but their employees still faced penalties for unreported income. You're absolutely making the right decision to decline this position. There are many legitimate outdoor education programs, nature schools, and environmental nonprofits that operate with proper tax compliance. These organizations typically hold 501(c)(3) status or operate as regular businesses, and they'll provide you with proper W-2s or 1099s for tax reporting. When you continue your job search, don't hesitate to ask potential employers direct questions about their tax structure and how they handle payroll reporting. Any legitimate organization should be able to clearly explain their tax status and provide proper documentation.