Whoa, I had no idea about the Recovery Rebate Credit! I definitely didn't get any stimulus money before because my parents claimed me. How do I check if I qualify for this? Would it be a significant amount?

You should qualify if you didn't receive the third stimulus payment (which was $1,400) and you're now filing as independent. Most tax software will ask you questions about this specifically - something like "Did you receive the third Economic Impact Payment in 2021?" It's definitely significant - it would be up to $1,400 added to your refund! Your tax software should help calculate this, but make sure you answer the questions about Economic Impact Payments carefully. If your parents received the payment for you as their dependent in 2021, you wouldn't qualify, but if no one received a payment for you, you likely will.

This is such an important distinction! I messed this up my first time filing too. I thought by selecting "Single" as my filing status, I was automatically indicating that I was claiming myself. But they're totally different questions on the tax forms.

This is super helpful, thank you! I didn't even know I could check what my employer reported to the IRS. Do these transcripts become available pretty quickly after employers submit them, or is there a delay? If my W2 just got generated recently, would it even show up there yet?

The wage and income transcripts are usually available by late May or June for the previous tax year, but there can be some lag time. If your employer truly just submitted your information recently, it might not show up yet. However, most employers submit their W2 information by the end of January, even if they're slow in getting the actual forms to employees. It's always worth checking - you might be surprised to find your information has been there all along, which could potentially strengthen your case about employer negligence for the penalty abatement request.

I don't think this advice is correct. Form 4852 is only if you NEVER received your W-2 or if it's incorrect. Since OP has the W-2 now, even though it's late, they should use the actual W-2 for filing, not the substitute form.

Thanks for pointing this out. I actually used 3 different platforms throughout the year. Do they all automatically send tax forms or do I need to request the statements?

Most platforms don't automatically send you win/loss statements - you need to request them specifically. They'll only automatically send W-2G forms for individual wins over $1,200. Each gambling site usually has a section in your account settings or help center that explains how to request your annual win/loss statement. Some platforms make these readily available to download from your account, while others require you to contact customer support. I recommend requesting these statements as soon as possible since it can sometimes take them a while to generate the documents, especially during tax season when everyone is asking for them.

This is a really good point. I made this mistake one year and actually ended up paying more in taxes by itemizing than I would have with the standard deduction.

TurboTax Self-Employed does have an estimated tax calculator, but in my experience it doesn't handle the annualized method very well. It more focuses on the equal payment method. I ended up using the IRS worksheets anyway. QuickBooks Self-Employed does a better job with variable income and quarterly calculations, but it's still not perfect for true annualization calculations.

Thankfully I don't have any capital gains stuff to worry about right now! It's just straight freelance income. If that changes I'll definitely get professional help.

Mixed straddle accounting is a whole different beast. You need to make an election to use it, and it has to be done by the due date of your return for the year the straddle was established. If you didn't make that election already, you probably can't use it retroactively.

That's good to know. I did make the election last year since I knew I'd be implementing these strategies. Do you know if using the mixed straddle accounting would solve the issue with reporting short positions that cross year-end? I'm trying to avoid the same reporting problems the original poster mentioned. I've read that mixed straddle accounting lets you avoid the mark-to-market rules for the 1256 contracts that are part of the straddle, which might simplify things.

Only options on "broad-based" indices qualify as Section 1256 contracts. Foreign indices generally don't qualify unless they're specifically listed by the IRS. If your foreign index has fewer than 10 stocks or if the options aren't regulated by the CFTC, they're probably just regular capital assets with standard short/long term treatment.