I'm kind of in a similar situation, maybe? I didn't file for a few years and now I'm trying to catch up. Does anyone know if I need to file for all the missing years before I can file for 2023? And also, maybe this is a silly question, but does the IRS eventually tell you if you were supposed to file but didn't?

@Andrew Pinnock You don't necessarily need to file all missing years before filing your current return - you can file them in any order. The IRS typically only requires you to file if you had income above the filing threshold for each year (which varies by year and filing status). As for your second question, the IRS usually doesn't proactively tell you that you should have filed unless they have records of income reported to them (like W-2s or 1099s) that would trigger a filing requirement. They might eventually send a notice if they detect unreported income, but this can take years. For catching up on multiple years, I'd suggest starting with the most recent year first since that's likely to have the biggest refund (if you're owed one), then work backwards. You can use prior year tax forms available on the IRS website. Just be aware that you can only claim refunds for the last 3 years - anything older than that, you lose the refund even if you were owed money.

Has anyone used H&R Block instead of TurboTax for handling a 1099-S for inherited land? I'm in the same situation but haven't filed yet, and wondering if their Deluxe version might handle this without needing to upgrade.

I went through this exact scenario last year with inherited farmland. A few key points that might help: First, don't panic about penalties - the IRS is generally understanding when forms arrive after you've already filed, especially 1099-S forms which are notorious for being late. You have plenty of time to amend once the forms become available. For the stepped-up basis calculation, I recommend calling the county assessor's office where the land was located. They often have historical records and can provide documentation of the property value around the time of death. In my case, they were able to give me a letter stating the assessed value, which I used as supporting documentation. One thing to watch out for - if this was agricultural land or had any special use designation, there might be additional considerations for the tax treatment. Also, since you mentioned it was partially owned by your mom, make sure you're only reporting your inherited portion of the proceeds, not the full amount on the 1099-S. The amendment process isn't as scary as it seems. When the forms become available (typically late February), you'll just need to file Form 1040-X along with Schedule D and Form 8949. TurboTax Premier will walk you through it step by step once it's available.

This is such a timely question! I'm dealing with the exact same situation on our small organic farm. One thing I learned the hard way is to make sure you're documenting the condition of your donated produce - the IRS wants to see that you're donating quality items, not just getting rid of culls or damaged goods. I keep a simple spreadsheet that tracks each donation with photos of the produce quality, our regular market prices that week, and copies of all food bank receipts. When we donated 200 lbs of heirloom tomatoes last month, I made sure to photograph them alongside our market price sign showing $4/lb for comparison. Also worth noting - if your food bank is part of a larger organization, make sure they're properly registered as a 501(c)(3). I had one small local pantry that wasn't properly registered and my accountant said those donations wouldn't qualify. Always ask for their tax-exempt documentation if you're unsure!

This thread has been incredibly helpful! As someone who just started a small CSA operation this year, I had no idea about the Schedule F implications for farm donations. I've been setting aside our "ugly" but perfectly good vegetables for the local food bank, thinking it was just a nice community gesture. Reading through all these responses, I realize I need to get much better organized with my documentation. I love the logbook idea from @d8db5f45b2f4 - I'm definitely going to implement that system before our next donation run. One follow-up question though: if we're donating items that we normally sell as "seconds" at a reduced price (like tomatoes with cosmetic blemishes), should we use our regular premium price or our discounted "seconds" price for the fair market value calculation? I want to be conservative and honest, but I also don't want to shortchange ourselves if the higher value is legitimate. Thanks everyone for sharing your experiences - this community is amazing for helping small farmers navigate these tax complexities!

Does anyone know if there are exceptions to getting a 1099-S? I sold a small parcel last year and never got one either but my tax guy said it wasn't needed in my case.

Just to add some clarity on the timing - while title companies have until January 31st to send you the 1099-S, most reputable companies will get it to you much sooner, often within 30-60 days of closing. Since you mentioned it's been over three weeks, I'd definitely recommend reaching out to them now rather than waiting. When you contact them, have your settlement statement handy with the closing date and property address. They'll likely ask for this information to locate your file. Also double-check that they have your current mailing address - address mix-ups are surprisingly common and could explain the delay. Even without the 1099-S in hand, start gathering your other documents now: original purchase paperwork, records of any improvements you made to the land, and your closing/settlement statement from the recent sale. You'll need all of this to properly calculate your capital gains anyway, so getting organized early will save you stress later.

As someone new to this community, I really appreciate all the detailed explanations here! I'm in a similar situation where I just signed a lease and was surprised by the W9 request. It's reassuring to see that this is actually a legitimate and common practice for landlords who keep deposits in interest-bearing accounts. The key takeaway I'm getting is that the W9 is just paperwork for the landlord's records - I don't need to do anything with it for my taxes unless I eventually receive a 1099-INT showing interest income of $10 or more. Since most security deposits don't earn that much interest in a single tax year (especially for newer tenants), it's likely a non-issue for most people. Thanks to everyone who shared their experiences and knowledge - this kind of practical tax advice from real situations is exactly what I was hoping to find in this community!

Welcome to the community! As someone who's dealt with similar rental tax questions, I wanted to add that it's also worth checking if your state has any specific laws about security deposit interest. Some states require landlords to pay a minimum interest rate (like 2-3% annually) while others allow them to keep whatever the account earns. Also, if you're planning to stay for 3+ years like you mentioned, that $1,750 deposit could potentially accumulate enough interest to trigger a 1099-INT in future years, especially if interest rates continue to rise. It's not something to worry about now, but good to keep in the back of your mind. The W9 process shows your landlord is being proactive about tax compliance, which is actually a good sign - it suggests they're running a professional operation and following proper procedures.