Has anyone tried using the IRS's own tax withholding estimator for this? I've been wondering if it works for self-employment income too or just W-2 jobs?

As someone who switched from W-2 to freelancing last year, I can relate to the confusion! One thing that really helped me was understanding that the 1040-ES isn't really a "filing" - you're just making payments with vouchers. You can actually make the payments online through EFTPS (Electronic Federal Tax Payment System) without even using the paper vouchers. Also, regarding TaxSlayer through Free File - yes, they do help calculate your estimated payments, but keep in mind that Free File is only for people making under $79,000 (for 2025). If your freelance business is growing significantly, you might exceed that threshold. One more tip: if this is your first year needing to make estimated payments, you might qualify for an exception to penalties even if you underpay, as long as you had no tax liability in the prior year. Worth looking into!

Anyone know if paying down the mortgage principal early counts toward your basis? I paid extra $12k toward my land loan to reduce interest.

Just wanted to add my experience for anyone else in this situation - I sold land last year and was able to include not just the original closing costs but also some fees I didn't initially think would qualify. Things like the lender's title policy, survey costs, and even the appraisal fee from my original purchase all counted toward my basis. One thing that really helped me was organizing all my documents chronologically - purchase closing statement, any improvement receipts during ownership, and then the sale closing statement. Having everything laid out made it much easier to identify what could be included in my basis calculation versus what were just regular ownership expenses. The key is distinguishing between costs that added to the property's value or were necessary for acquisition (which increase basis) versus ongoing expenses like property taxes, insurance, or maintenance (which don't). When in doubt, keep the receipt and document it - it's better to have records you don't need than to miss legitimate deductions.

What tax form do you use to report land sale? I sold some acres last year and my tax software confused me.

One thing that might help you is to track down your original settlement statement (HUD-1 or Closing Disclosure) from when you purchased the land 5 years ago. That document will itemize all the closing costs you paid, making it much easier to determine which ones can be added to your basis. From my experience, most of the fees listed on that settlement statement can be included - things like title insurance, attorney fees, recording fees, survey costs, and transfer taxes. The main exceptions are usually prepaid items like property taxes and homeowner's insurance (though with raw land you probably didn't have insurance). Also, don't forget that any improvements you made to the land over those 5 years (like adding utilities, grading, fencing, etc.) can also be added to your basis. Keep good records of everything - the IRS likes documentation if they ever come asking questions!

As someone who's been through similar joint ownership complications, I'd strongly recommend getting a written co-ownership agreement in place ASAP, even though you already have the deed. This should specify your 60/40 economic split, how decisions get made about the property, what happens if one person wants to sell, and how you'll handle major repairs or improvements. For the tax side, your current approach of reporting based on your actual investment percentages (60/40) is generally correct - just make sure you're consistent with both income AND expenses in that same ratio. The joint tenancy language on the deed is more about legal ownership rights than tax reporting. One thing to watch out for: if either of you dies, the surviving owner gets a "stepped-up basis" on the deceased owner's share, which can be really beneficial for capital gains purposes. But if you're young and healthy, the inability to easily sell just your portion (as others mentioned) might be more of a concern than the survivorship benefits. Consider whether converting to tenants in common or setting up an LLC might give you more flexibility while you're both alive.

The stepped-up basis benefit Ravi mentioned is huge and often overlooked! When one joint tenant dies, the surviving owner gets a stepped-up basis on the deceased person's share equal to fair market value at death. This can save thousands in capital gains taxes later. However, there's also the gift tax angle to consider with your 60/40 arrangement. Since the deed shows equal ownership but you're splitting income 60/40, the IRS could potentially view the extra 10% going to the person who contributed less as a gift each year. Usually not an issue unless you're dealing with large amounts, but worth documenting your actual contributions clearly. For liability protection, definitely look into an LLC or at minimum get umbrella insurance. Joint tenants are each 100% liable for the entire property - if someone gets hurt and sues, they can go after either owner's personal assets regardless of your 60/40 economic split.

Code 201 is more of a yellow flag than a red flag - it just means they're making an adjustment and will send you a notice explaining why. I've seen this code three times over the years, and twice it was actually in my favor (they found credits I missed). The key thing is to wait for the actual notice letter, which usually arrives within 1-2 weeks of the code appearing. Don't stress too much about it - unlike some other codes that indicate holds or delays, 201 just means they're communicating with you about a change to your account. Keep checking your mailbox and you'll have your answer soon enough.

I've dealt with code 201 a few times over the years, and honestly it's usually not as scary as it first appears. The waiting period between seeing the code and getting the actual letter is always nerve-wracking, but in my experience it's been about 50/50 whether the adjustment was in my favor or not. One time they caught that I had accidentally double-entered a charitable deduction, so they reduced my refund. Another time they found a child tax credit I was eligible for but somehow missed. The most important thing is that code 201 means they're being transparent about making a change - it's when you DON'T see codes that you might have bigger problems brewing. Just keep an eye on your mailbox and try not to overthink it until you get the official explanation.