7 So what form do I need to fill out for this? Is it complicated?

22 You'll need to fill out Schedule D (Capital Gains and Losses) and Form 8949 (Sales and Other Dispositions of Capital Assets). The 1099-B from Cash App contains all the information you need to complete these forms. It's not particularly complicated for simple transactions like yours. Most tax software, even free versions, will walk you through entering the information from your 1099-B and will automatically fill out these forms for you. The software will ask for details like purchase date, sale date, cost basis, and proceeds - all of which should be on your 1099-B.

24 This is the right answer. I had a similar situation last year. Reported tiny gains, took maybe 5 extra minutes in TurboTax free edition, paid no extra fees, and had zero issues. All this worrying is more work than just filing it correctly.

4 Exactly! People get so worried about tax stuff when the solution is often simple. In this case: report it properly, pay the fraction of a penny you might owe, and sleep well knowing you're compliant. If the IRS sent you a form, they know about it - just include it in your return.

But what if there is a huge difference? My assessment from January valued the land at 120k, but the July one (closer to when I started renting) suddenly jumped to 180k due to some county-wide reassessment. That's a big difference in depreciable basis!

In that case, where there's a substantial difference that materially affects your tax liability, you should definitely go with the most accurate assessment closest to your placed-in-service date. The July assessment would be appropriate since it reflects the most current valuation when you began renting. For significant changes like you described, it's also worth consulting with a tax professional who specializes in real estate to ensure you're taking the right approach. You might even want to get a private appraisal that specifically breaks out the land value as of your placed-in-service date to have solid documentation if the IRS ever questions your depreciation calculations.

This is good advice! My HUD-1 settlement statement had this breakdown too. Made it super easy come tax time. Always check your closing docs first before digging through property tax records.

16 Do you have a link to this? I tried searching but came up with several different resources and I'm not sure which one you're referring to.

7 Sorry I should have included the link! It's called "Tax Procedure" by Morgan and is available through the University of Minnesota Scholarship Repository. Just Google "Morgan Tax Procedure Minnesota" and it should be the first result. The direct PDF is a bit hard to link, but that search should get you there. The most recent edition covers all the TCJA changes and has excellent citations if you want to dive deeper into specific sections of the tax code.

12 Bloomberg's materials are extremely comprehensive but probably not where you want to start if you're new to tax law. They're really designed for practicing tax attorneys and CPAs who already have a strong foundation. I'd recommend starting with something more accessible to build fundamentals, then using Bloomberg as a reference resource when you need deep dives into specific topics.

I never thought to check that! We do use Workday actually. Is this something in the benefits section or somewhere else? I'll have to poke around tomorrow. If I could set preferences that would be awesome.

Check under the Payroll section in Workday. Look for something called "Tax Withholding" or "W-4 Elections." Most versions have a withholding calculator where you can play with different scenarios. Some even have a slider where you can choose between maximizing paychecks (0 refund) or getting a specific refund amount. It's usually in the same place where you would update your W-4 information. The calculator is pretty helpful because it shows how each change affects both your paycheck and your expected refund. If you don't see it, your HR department can tell you if this feature is enabled for your company.

This is actually a myth that needs to die. For most normal people, the "interest" you'd earn on the extra $20-40 per paycheck is minimal compared to the psychological benefit of getting a larger refund. Most people don't invest that small difference anyway.

You're missing the bigger financial picture. Even small amounts add up significantly over time, especially with compound interest. An extra $40 per paycheck is $1,040 annually that could be in your investment accounts growing instead of sitting with the IRS. But more importantly, having access to your full earnings gives you financial flexibility throughout the year. That money could go toward paying down high-interest debt, building an emergency fund, or investing in retirement accounts with tax advantages. It's about having control of your own money rather than voluntarily restricting access to it. For people struggling with cash flow issues, every dollar in their regular paycheck matters.

Thanks for mentioning the SEP IRA option! Do you know what the contribution limits are compared to the Solo 401k? And is it true there's less paperwork involved? The Form 5500 requirement for Solo 401ks once you hit $250k sounds like a potential headache.

For a SEP IRA, you can contribute up to 25% of your net self-employment income with a maximum of $66,000 for 2023. With a Solo 401k, you can contribute $22,500 as an employee plus that same 25% of income as the employer contribution, still capped at $66,000 combined. The paperwork difference is significant. With a SEP, there's no annual filing requirement regardless of account size - just set it up once and make contributions. Solo 401ks require Form 5500-EZ filing once assets exceed $250,000, which isn't super complicated but is an extra annual task. For many small business owners, the simplicity of a SEP outweighs the potential for slightly higher contributions with a Solo 401k.

Did you have to start running payroll for yourself to contribute to the Solo 401k? That's the part that confuses me with my LLC.