Has anyone successfully used TurboTax for handling RSUs? I've been getting different answers each year and I'm not sure if it's calculating everything correctly.

This is such a common problem with RSU taxation! I went through the exact same issue and found that many companies struggle with properly reporting RSU withholding on W-2s, especially when vesting happens near year-end. One thing that helped me was creating a simple spreadsheet tracking each vesting event throughout the year. For each vest, I recorded: the vesting date, number of shares that vested, FMV per share on that date, number of shares withheld for taxes, and the dollar value of those withheld shares. At year-end, I could easily calculate the total tax withholding that should appear in Box 2 of my W-2. Also, don't overlook Box 12 on your W-2 - sometimes companies report additional information about RSU withholding there with codes like "V" or other employer-specific codes. And definitely check if your company provides a supplemental RSU tax statement - mine sends one each January that breaks down all the vesting events and associated tax implications for the year. The fact that you've had consistent tax bills for 3 years strongly suggests there's a systematic reporting issue. I'd recommend documenting everything before approaching HR so you can present them with specific numbers rather than just a general concern.

did you check if you have any freezes or holds? sometimes they dont show up obvious on the transcript but theyre there

A negative balance definitely means the IRS owes you money! With your tax liability at $0 and that negative balance, you likely received refundable credits like the Child Tax Credit or Earned Income Credit that created the overpayment. The delay could be due to identity verification, income verification, or just processing backlogs. I'd recommend calling the IRS refund hotline at 1-800-829-1954 to check if there are any issues holding up your refund. You can also try calling early morning (7-8am) for better chances of getting through!

I ran into this exact issue last year! The key question is: who has the payment relationship with the freelancer? With Fiverr, YOU pay FIVERR, and then FIVERR pays the FREELANCER. So Fiverr is responsible for issuing any required tax forms to the freelancer, not you. You're basically paying for a service from Fiverr the company, not directly employing the freelancer. But beware! If you ever take the relationship off-platform (like if you hire a Fiverr freelancer directly after working with them on the platform), then you DO need to issue a 1099-NEC if you pay them $600+ in a year. I learned this the hard way lol.

Just wanted to chime in as someone who processes a lot of 1099s for small businesses - everyone here is giving you solid advice! When you use Fiverr, you're essentially purchasing services from Fiverr Inc., not directly contracting with individual freelancers. The $600 threshold for 1099-NEC reporting only applies to direct business relationships where you're paying independent contractors yourself. Since Fiverr acts as the middleman collecting payment from you and then paying their freelancers, they assume the responsibility for any required tax reporting. Your $2,800 in Fiverr purchases should just be treated as regular business expenses - keep your receipts from Fiverr for your records, but no 1099s needed on your end. The freelancers will receive their tax documents directly from Fiverr if they meet the reporting thresholds. One tip: make sure you're categorizing these expenses correctly in your books as "Professional Services" or "Contract Labor" so you can deduct them properly as business expenses!

As someone who's been in real estate development for 15 years, I'd strongly recommend consulting with a CPA who specializes in real estate. The dealer vs investor status isn't always clear-cut, and I've had projects where we were able to make strong arguments for investor treatment even though we were developing properties.

I've been through this exact situation with my development projects. One key factor that hasn't been mentioned yet is the frequency and scale of your development activities. The IRS looks at whether real estate development is your primary business or just occasional transactions. If you're doing multiple developments per year with the intent to sell, you're almost certainly going to be classified as a dealer. For dealer status, you'll need to report expenses as they occur on Schedule C - this includes your holding costs, permits, materials, labor, etc. The profit gets treated as ordinary income subject to self-employment tax, which can be quite significant. However, there's one strategy worth exploring: if you occasionally hold a property for rental purposes before selling (even just 1-2 years), you might be able to argue for dual-purpose treatment on some properties. This requires very careful documentation of your intent from the beginning of each project. I'd definitely echo the advice about getting a real estate-focused CPA. The nuances here can save or cost you thousands in taxes, and the rules have gotten more complex with recent tax law changes.

Great question! I was in a similar situation a few years ago and can confirm what others have said - the math is $48,350 (0% LTCG bracket) + $15,950 (standard deduction) = $64,300 total you can realize tax-free as a single filer with no other income. One thing I'd add that hasn't been mentioned much - be really careful about the timing of any sales if you're close to that limit. Since you're unemployed now, this is actually the perfect time to do this strategy. But if you think you might get a job later this year, remember that even a few months of employment income could push you over the 0% bracket. Also, don't forget to keep good records of your cost basis and purchase dates. The IRS has been cracking down on people who can't properly document their long-term holding periods. I learned this the hard way when I had to dig through old brokerage statements during an audit. The strategy you're considering is completely legitimate and can save you thousands in taxes - just make sure you execute it carefully!

This is exactly the kind of strategic tax planning that can make a huge difference during unemployment! One additional consideration I'd mention is to be mindful of any estimated tax payments you might need to make if you do realize significant gains. Even though your federal tax liability might be zero, if you have substantial capital gains (like the $60k+ range being discussed), you might still need to make estimated payments to avoid underpayment penalties - especially if you had tax liability in prior years. The IRS safe harbor rules can be tricky to navigate when your income profile changes dramatically. Also, since you're job hunting, consider the timing of when you might start earning employment income again. If you land a job in Q4 of this year, even a few months of salary could push some of your capital gains into the 15% bracket. You might want to front-load your investment sales earlier in the year while you're certain about your income situation. The unemployment period is actually a unique opportunity for this type of tax optimization that many people don't think to take advantage of. Just make sure you're not selling investments you might need to buy back soon - you don't want to trigger wash sale rules if you're planning to reinvest the proceeds.