If you sold for $21,500 and bought for $12,000, don't forget that's a $9,500 profit which is subject to capital gains tax! Since you held it more than a year, you'll get the lower long-term rate (0%, 15%, or 20% depending on your income) instead of your regular income tax rate.

One thing that hasn't been mentioned yet is the Net Investment Income Tax (NIIT). If your modified adjusted gross income exceeds certain thresholds ($200,000 for single filers, $250,000 for married filing jointly), you may owe an additional 3.8% tax on your capital gains from the land sale. This is separate from the regular capital gains tax and catches a lot of people off guard. The good news is that with a $9,500 gain, it's unlikely to push most people over those income thresholds unless they already have substantial other income. But it's something to be aware of when planning your tax strategy, especially if you're considering selling other investments in the same year. Cash App Tax should automatically calculate this if it applies to your situation, but it's worth understanding so you're not surprised by an unexpected tax bill.

I just wanted to add one more perspective as someone who recently went through this exact situation. I received a CP14 notice for $775 and was initially terrified about making the payment online, but after reading all the excellent advice in this thread, I decided to go the electronic route. The process was exactly as everyone described: go to irs.gov/payments, select "Pay Your Tax Bill," choose "Notice" as the payment reason (this is crucial - not "Tax Return"), select your tax year (2023), and enter the exact amount from your CP14. I used the Direct Pay option to avoid any fees. One thing I'd add that really helped me was setting up my IRS online account beforehand so I could track the payment status. This gave me peace of mind because I could verify that the payment was properly applied within 48 hours. The entire payment process took less than 15 minutes, and I got immediate confirmation. What really convinced me to pay online was realizing that my notice was accumulating about $2.50 per day in interest. Even a one-week delay from mailing a check would have cost me an extra $17.50, not to mention the stress of wondering if it got lost in the mail. The electronic payment stops interest accumulation immediately on the date you submit it. For anyone still hesitating - the online option really is the way to go for CP14 notices. Just make sure to screenshot your confirmation page and keep that confirmation number safe!

I just wanted to share my experience as someone who was in the exact same situation a few months ago with a CP14 notice. I was completely overwhelmed at first, but the online payment process really is much simpler than it seems! Here's what worked for me: Go to irs.gov/payments and click "Pay Your Tax Bill." The key thing is to select "Notice" as your payment reason (not "Tax Return" - this tripped me up initially). Then choose 2023 as your tax year and enter exactly $850 as shown on your CP14. I'd definitely recommend using the Direct Pay option from your bank account since it's free and processes quickly. You'll get a confirmation number immediately, which stops the interest from accumulating right away. The IRS considers your payment made on the date you submit it online, not when the money actually comes out of your account (which takes 1-2 business days). One tip that really helped me: take a screenshot of your confirmation page! The payment might not show up in your IRS online account for 24-48 hours due to system processing, but having that confirmation number gives you proof and peace of mind. I was initially scared about paying online, but it ended up being so much faster and cheaper than mailing a check. My balance showed as paid within 2 days, and I avoided all the extra interest that would have accumulated during mail processing time. You've got this!

I had a similar experience with Woodforest last year - DDD of 3/15 and it hit my account at exactly 3:17am that morning. Not a minute earlier! I learned not to get my hopes up for early deposits with them. They're super reliable but stick to the exact date. Since you have bills due on the 27th, you should be good to go with a 2/26 DDD. Pro tip: if you have mobile banking, turn on push notifications so you'll know the second it hits without having to obsessively check your account like I did 😂

I've had Woodforest for about 3 years now and they're super consistent with tax refunds - always hits at exactly 3am on the DDD, never early. I know it sucks waiting when you have bills coming up, but you can definitely count on seeing that money in your account right at 3am on 2/26. I'd recommend setting up mobile alerts so you don't have to stay awake checking! Also, since your electric bill is due the 27th, you'll have plenty of time to pay it once the deposit hits. Woodforest may not be one of those banks that releases funds early, but at least they're reliable!

I'm dealing with a similar relocation repayment situation right now and this thread has been incredibly helpful! I wanted to add one more consideration that might be relevant - if you received any interest or penalty charges as part of your repayment agreement, those are generally NOT eligible for the Section 1341 treatment. Only the principal amount that you're repaying (the original relocation benefits) qualifies for the claim of right relief. Any interest or late fees you might be paying should be treated separately, and unfortunately those typically aren't deductible for individual taxpayers under current tax law. Also, I noticed you mentioned using TurboTax for the practice amendment. While that's a good start, be aware that TurboTax's handling of Section 1341 situations can be limited, especially for complex scenarios involving multiple states. You might want to double-check their calculations manually or consider having a professional review the work before you submit, even if you do most of the prep yourself. The timeline you're looking at (filing in May with an extension) actually works in your favor since it gives you time to get everything right and deal with any employer pushback on the FICA issue before you file.

I went through almost the exact same situation in 2023 with a $14k relocation repayment, and I can share a few things that might help based on my experience. First, your TurboTax estimate of $3.3k federal refund sounds about right for a $16k repayment if you were in the 22% bracket originally. I ended up getting back about $2.8k on my $14k repayment using the Section 1341 credit method. For the FICA tax issue with your former employer, I found that sending them a formal written request (not just phone calls or emails) with the specific tax code references made a big difference. I included IRC Section 3402(d) and Publication 15 guidance about their obligation to file Form 941-X. Once they realized this was a legitimate tax requirement and not just me asking for a favor, they processed it within about 6 weeks. One thing to watch out for - make sure you're clear on whether your $16k repayment is the gross amount or net amount. If it's gross (which sounds like it is based on your description), then you're definitely on the right track with pursuing the amendment. If it were net, the tax recovery wouldn't be as straightforward. The May filing timeline with an extension actually worked well for me too. It gave me enough time to get all the documentation together and resolve the employer FICA issue before filing. The IRS processed my amendment in about 10 weeks after submission, which was faster than I expected.

One thing nobody's mentioned - if you do the 1031 exchange and buy a property near campus, but have your son living there, you need to be VERY careful about personal use rules. The IRS could potentially disallow the entire exchange if they determine the property wasn't held primarily for investment purposes. Generally, you need to charge fair market rent to family members to maintain the investment property status. Having your son manage the property for a reasonable fee is fine, but giving him free or reduced rent could jeopardize both the 1031 exchange and your ongoing rental property deductions.

This is a really thoughtful approach to college planning! I'm in a similar situation with my daughter heading to college next year, and I've been researching these same strategies. One additional consideration for the 1031 exchange route - make sure you factor in the local rental market dynamics near potential colleges. College town rental markets can be quite different from typical residential rentals. They often have seasonal vacancy periods (summer), higher turnover, and sometimes stricter local regulations about student housing. Also, regarding your question about imputed income for rent-free housing - generally, providing free housing to your child wouldn't create taxable income for them as long as it's considered support rather than compensation. However, as others mentioned, if you're claiming rental property deductions, you need to charge fair market rent to maintain the investment property status. Have you considered setting up a formal lease agreement with your son at fair market rates, but then gifting him money separately to cover the rent? This keeps the rental income legitimate while still effectively providing the housing benefit. You'd need to stay within annual gift tax exclusion limits, but it might be a cleaner approach from a documentation standpoint. The property management compensation route definitely works if structured properly - just make sure the duties and compensation are genuinely reasonable compared to what you'd pay a third party.