Make sure you're using good tax software for this! I messed up my 1099-R reporting last year by trying to do it manually and ended up with a CP2000 notice from the IRS. The penalty plus interest was painful.

I had a similar situation last year with multiple 1099-Rs and early withdrawal penalties. One thing that really helped me was creating a simple spreadsheet to track everything before entering it into my tax forms. I listed each 1099-R with the amounts from boxes 1, 2a, and 4, then calculated the 10% penalty on just the box 2a amounts. This made it much easier to double-check my work before filing. Also, don't forget that if you have state income tax, you'll need to check your state's rules too. Some states follow the federal early withdrawal penalty rules, while others have their own calculations or don't impose the penalty at all. My state actually had a lower penalty rate than the federal 10%, which was a pleasant surprise when I discovered it. The key is being methodical about it - the federal withholding from all your 1099-Rs gets combined with your W-2 withholding on line 25b, and the penalty calculation is straightforward once you focus on just the taxable amounts in box 2a.

Has anyone considered using a 1031 exchange instead? If the property is eventually going to be an investment property, you might be able to defer those capital gains entirely!

One important consideration that hasn't been fully explored - if you're planning to live in this property as your primary residence initially, you should also think about the capital gains exclusion for primary residences down the road. If you live there for at least 2 of the next 5 years, you could potentially exclude up to $250k (single) or $500k (married) of capital gains when you eventually sell the property. This could be a powerful strategy: realize the stock gains now (ideally split across tax years as others suggested), use that money to buy the property, live there as your primary residence for the required period, then potentially sell tax-free later. The timing requirements are strict though - you need to own AND live in the home for at least 2 years out of a 5-year period. Also, since you mentioned considering this as an investment property eventually, be aware that if you convert it from personal residence to rental property, you'll need to deal with depreciation recapture when you sell, which is taxed at up to 25%. But the primary residence exclusion could still apply to the appreciation portion if you meet the use requirements.

Has anyone actually received any penalties for filing an incorrect 1099-NEC? I submitted one with the wrong amount last year (off by about $2,000) but never bothered to correct it since the contractor said they'd just report the correct income on their taxes anyway. Now I'm worried I should have filed a correction.

I want to emphasize what Natasha said about penalties - you really should file that correction ASAP! I had a client who ignored a $1,500 error on a 1099-NEC thinking it wasn't a big deal, and the IRS hit them with a $280 penalty when they discovered it during an audit two years later. The penalty structure is based on when you correct it: - $50 per form if corrected within 30 days - $110 per form if corrected by August 1st - $280 per form if corrected after August 1st or not corrected at all Even though your contractor might report the correct income, the IRS matches 1099s to tax returns electronically, and discrepancies can trigger notices or audits for both you and your contractor. It's much easier to just file the correction now than deal with potential headaches later. You can still use the IRIS system to file the correction even though it's been a while - just mark it as "Corrected" and include the accurate information.

Target employee here! I just got my W2 on My Tax Form this morning around 2 AM. I've been checking obsessively too lol. From what I've noticed working there for 3 years, Target usually uploads W2s in waves based on your employee number or store region. The first batch typically goes up around January 20th, with most everyone having theirs by January 28th. If you're still not seeing yours by January 29th, definitely call the Target HR hotline - sometimes there are issues with address changes or electronic consent that can delay individual W2s. Also make sure you're logged into the right My Tax Form account (the one linked to your Target employee profile). Hope this helps ease some of the anxiety!

As someone who works in payroll processing, I can confirm what others have mentioned about the January 31st deadline being federal. However, I wanted to add that if you're really anxious about getting started early, you can actually begin preparing your tax return using your final paystub of the year. The year-to-date totals on your last paystub are usually very close to what will appear on your W2. Just gather your final paystub from December and you can estimate your federal and state tax withholdings, gross wages, and other deductions. Most tax software allows you to input estimated numbers and then update them later when your official W2 arrives. This way you can get a head start on organizing your other tax documents (1099s, receipts, etc.) while waiting for Target to upload your W2 to My Tax Form. Also, if you haven't already, make sure you're signed up for electronic delivery in your Target employee portal - sometimes people miss this step and then wonder why their W2 isn't showing up online when it's actually being mailed to an old address.

Just want to add some clarity here since I see some conflicting info in the thread. The IRS uses these transaction codes consistently: - Code 01 = Single - Code 02 = Married Filing Jointly - Code 03 = Married Filing Separately - Code 04 = Head of Household - Code 05 = Qualifying Widow(er) @Ava Martinez - If your 2022 and 2021 returns show code 05, you were filing as Qualifying Widow(er), not Head of Household. This status is available for up to 2 years after your spouse's death (if you have a qualifying dependent). If you got divorced rather than widowed, you may have filed incorrectly in those years. I'd recommend reviewing your actual tax returns to confirm what filing status you used, as this could impact your tax liability for those years. The change to code 01 (Single) for 2023 makes sense post-divorce, but definitely double-check those earlier returns to make sure you used the right status.

This thread has great info! Just wanted to add that if you're unsure about your previous filing status, you can request copies of your actual tax returns (not just transcripts) using Form 4506. The transcripts show the codes the IRS processed, but your original returns will show exactly what filing status you selected when you filed. This is especially important given the questions about whether you filed as Qualifying Widow(er) vs Head of Household in those earlier years. The return copies cost $43 each but might be worth it for peace of mind, especially if you're concerned about potential filing errors that could trigger penalties or interest.