Does this apply to supplemental property tax bills too? I thought those were different since they're retroactively assessing tax for periods before the bill was created.

Supplemental property tax bills are actually a good example of properly assessed taxes. Since the supplemental bill has already been issued with specific amounts and due dates, it has been officially assessed by the tax authority. The concern I was mentioning applies more to trying to prepay future regular property tax installments that haven't been billed yet. With supplemental bills, both installments are typically assessed at the same time when the bill is issued, even though the second payment is due months later. So paying both installments in the same tax year for deduction purposes is usually fine with supplemental bills.

Yes! We challenged our supplemental bill and got it reduced by about $1,800. The key is to file the appeal quickly - most counties have a deadline of 60 days after receiving the bill. We provided our closing documents showing the actual purchase price and they adjusted it.

But isn't it kind of satisfying to get a big refund check? I use it as a forced savings account lol. I know it's not optimal but it works for me.

I totally get the psychological appeal of a big refund check! Many people do use it as a forced savings method, and if that works for your financial habits, there's some value there. The downside is you could be putting that money to work throughout the year - paying down debt, investing, or addressing immediate needs. With inflation eating away purchasing power, money you get back in April is worth less than if you'd had it in your paycheck throughout the previous year.

I work at a tax prep office (not an expert tho) and we DO see refunds get delayed when there are unusually large overpayments. IRS systems flag them for manual review because large refunds can be signs of fraud. Not saying you've done anything wrong, but that might explain the delay.

Thanks for clarifying. That's gonna be a nightmare with how many transactions I've made. Does the IRS really expect average people to track all this? Do you think there's any wiggle room for small transactions under a certain amount?

The IRS does expect all transactions to be reported regardless of size. There's no minimum threshold that exempts you from reporting crypto transactions, unlike some other areas of tax law. That said, practically speaking, many tax professionals use software that can consolidate similar transactions, especially numerous small ones. The important thing is that your overall tax liability is accurately reported. If you're dealing with hundreds of small transactions, I'd strongly recommend using specialized crypto tax software that can import your transaction history directly from exchanges and wallet addresses. This can save countless hours of manual data entry while ensuring compliance.

I tried using TurboTax for my crypto last year and it was a disaster for anything beyond basic buying/selling. Had to switch to a dedicated crypto tax software halfway through. For gambling specifically, they have you report winnings under "Other Income" on Schedule 1, but they don't handle the crypto withdrawal part well at all.

Thanks for the response. That's what I was afraid of. Did you end up using a different tax software altogether or did you just supplement TurboTax with something else for the crypto part?

I've used FreeTaxUSA for my 1099 income for years. It's WAY cheaper than TurboTax and handles Schedule C and all the self-employment forms just fine. TurboTax constantly tries to upsell you to their more expensive "self-employed" version.

I've heard this "replacement cost" approach too, but what about when you're wearing multiple hats? In my small S-Corp, I'm the CEO, marketing department, sales, and janitor. Should I be calculating different reasonable salaries for each role?

That's a great question and something I struggled with too! My accountant advised documenting the approximate percentage of time spent in each role, then calculating a blended "replacement cost." For example, if you spend 30% of time on high-level strategy (CEO work), 50% on billable service work, and 20% on admin tasks, you'd calculate what each of those roles would cost to replace, multiply by the percentage of time, and add them up. This approach acknowledges that not all your time is spent on the highest-value tasks, which helps justify a lower overall salary while still being "reasonable.

The minimum wage approach can work as a starting point, but it depends on your specific situation. For highly skilled professions (doctors, lawyers, consultants, etc.), the IRS would likely challenge minimum wage as "reasonable" since the market rate for those services is much higher. However, for businesses with tight margins in less specialized fields, documenting your hours and paying at least minimum wage could be defensible - especially if you clearly document your business circumstances and why this approach makes sense for your situation. The key is having that documentation ready if questioned.