Why not just call the farmer directly and ask? Seems like a lot of guessing going on when the person issuing the 1099 could clarify exactly why they're sending it to you instead of your grandparents.

Good thinking to call the farmer directly! That's definitely the simplest approach. When you do call, make sure to ask specifically: 1) Why the 1099 is being issued to you instead of your grandparents who own the land, 2) Whether this was intentional or if there's been a mistake in their records, and 3) If it was intentional, what the arrangement is between you, your grandparents, and the farmer. Also ask the farmer to explain in writing (even just via email) what services or arrangement the payment covers - this will be helpful for your tax records regardless of how you end up reporting it. Sometimes these rural arrangements can be informal and based on handshake agreements that weren't clearly documented, so getting clarity now will save you headaches later. Once you have that information, you'll know whether you need to report this as rental income, other income, or if the 1099 needs to be corrected entirely.

Don't overlook the testing period requirements if you do use the last month rule for the portion you're eligible for! I made this mistake. I contributed using the last month rule, then changed jobs and lost my HDHP coverage 8 months into the following year. Had to pay taxes PLUS a 10% penalty on the "accelerated" portion of my contribution. The IRS calls it "failing the testing period" and they definitely enforce it.

Based on your situation, you'll need to use a prorated calculation rather than the full last month rule benefit. Since you contributed to a general-purpose FSA from January through June, you were HSA-ineligible during that period, even though your FSA and HSA coverage didn't overlap. Here's how to calculate your maximum contribution: - Your wife: Individual limit for 6 months (Jan-June) - Both of you combined: Family limit for 6 months (July-December) The calculation would be: (Individual annual limit ÷ 12 × 6) + (Family annual limit ÷ 12 × 6) For 2024, that's roughly: ($4,150 ÷ 12 × 6) + ($8,300 ÷ 12 × 6) = $2,075 + $4,150 = $6,225 total You cannot use the last month rule to contribute the full $8,300 family amount because your FSA participation made you ineligible for HSA contributions during those months, regardless of the fact that they didn't overlap. This is a specific IRS limitation that trips up many people in FSA-to-HSA transitions. Make sure to keep documentation of your insurance effective dates and FSA contribution cessation for your records!

Did you already have a Credit Karma account? That can cause problems too

Check if you have any existing disputes or alerts on your credit report that might be blocking the verification. Also, make sure your name and address in TurboTax exactly match what's on your credit file - even small differences like "St" vs "Street" can cause failures. You might need to call TurboTax support directly since this seems to be affecting multiple people.

Pro tip: Sign up for text alerts with SBTPG. At least youll know the second they get it

Just wanted to add that you can also check your IRS transcript on the IRS website to see exactly when your refund gets processed and released. It'll show a 846 code when the money actually gets sent out to SBTPG. Usually takes them 1-2 business days after that to deposit it in your account. The transcript is free and way more detailed than WMR!

Dumb question maybe, but why are you setting up an S-corp if you're just a single-member LLC? I've heard the tax savings aren't worth the headache until you're making well over $100k profit. Now you've got this whole retirement plan complication too.

Your analysis looks spot-on! You're absolutely correct about the SEP-IRA being your best option for 2023. Just to reinforce what others have said - with your $95,000 W-2 wages from the S-corp, you can contribute exactly $23,750 to a SEP-IRA (25% of compensation), and you have until March 15th to both establish and fund it. One thing I'd add: make sure you're documenting your "reasonable salary" justification well. The IRS scrutinizes S-corp salaries, especially when the salary seems low relative to distributions. Your $95k salary on $405k in sales might raise eyebrows, so having solid documentation about industry standards for engineering consultants will be important. For 2024, definitely go with the solo 401k - the flexibility is unmatched. You'll be able to contribute up to $69,000 total ($23,000 employee + up to $46,000 employer contribution based on your salary). Just remember to establish it by December 31, 2024, though you have until the tax deadline to actually fund it. Also worth noting: if your income continues to grow, consider bumping your salary a bit in 2024. Higher salary = higher retirement contribution limits, and it might help with IRS reasonableness tests.