1 That's actually what I'm planning to do come January when I start my new full-time job, but my concern is about the remaining months of this year where I'm only self-employed. Do you know if there's a minimum threshold of income where quarterly payments become required?

22 The general rule is that you need to make estimated tax payments if you expect to owe $1,000 or more in taxes when you file your return. So if your self-employment income between now and December will result in less than $1,000 in additional tax, you might not need to make quarterly payments. Another consideration is that penalties are calculated based on each quarterly period separately. Since you started self-employment recently, you may only need to worry about the remaining quarters of this year rather than all four periods.

4 I used it last year and found it overestimated what I needed to pay each quarter. I think it doesn't factor in all deductions until you complete your final return. I switched to QuickBooks Self-Employed which gives me more real-time estimates based on my actual expenses and income.

That's terrifying! Did you end up having to pay NY taxes even after moving to Florida? I'm wondering if I should just do this properly from the start and actually spend most of my time in Florida, or if it's not worth the hassle.

I managed to prove I was in Florida for most of the year so I didn't end up owing NY taxes, but it was incredibly stressful and time-consuming. I had to hire a tax attorney which cost about $7,000. The audit lasted over 8 months. If you're serious about changing residency, I'd absolutely recommend doing it properly from the start. The "183 day rule" is just the beginning - you need to genuinely relocate your life. If you're only planning to be in Florida 3-4 months while keeping your Illinois apartment as your main home, you'll almost certainly still be considered an Illinois resident for tax purposes. The penalties for incorrect filing can include back taxes, interest, and significant penalties. Some states can look back several years if they believe you've been improperly claiming non-residency. It's really not worth trying to game the system unless you're actually making a legitimate move.

My company says they can only have me registered in one state at a time for payroll purposes. Would that cause problems if I'm splitting time between two states?

That's a common limitation with many employers, and it can definitely create complications. If your company will only register you in one state for payroll purposes, but you're actually working from multiple states, you may end up with a mismatch between your tax withholdings and your actual tax obligations. If you establish Florida as your legal domicile but still work from Illinois part of the year, you might still owe Illinois taxes on income earned while physically working there, even if no Illinois taxes are being withheld from your paychecks. This would mean you'd need to track your working days in each location very carefully and potentially file part-year or non-resident returns in Illinois, paying additional taxes out of pocket rather than through withholding. This is why many remote workers who split time between states end up committing fully to their no-tax state residence, minimizing time in high-tax states to avoid these complications. The paperwork and compliance requirements can quickly become very complex when you're splitting time.

Would they really go after someone for less than a pound in unpaid tax though? Seems like it would cost them more to send the letter than they'd get back.

It's not about the amount, it's about the principle. HMRC systems are increasingly automated and can pick up discrepancies between what platforms report and what you declare. My friend didn't get in serious trouble, but did have to file an amended return and pay a small penalty that was way more than the actual tax due. The real issue isn't the £2 over - it's that once you're over the allowance threshold, technically the full amount becomes declarable (though you still get to claim the £1000 allowance against it). HMRC might not chase 80p, but they might question why £1002 of income wasn't declared at all.

That's not correct. The £1000 trading allowance absolutely applies to self-employed work including Uber. Being self-employed doesn't change the allowance - that's precisely what the trading allowance is for: small amounts of self-employed/trading income.

But my Coinbase 1099 is missing a bunch of transactions from before 2023. Does that mean I'm screwed?

You're not screwed, but you do need to account for those missing transactions. Exchanges are only required to report transactions from certain years forward, but that doesn't exempt you from reporting everything. For transactions not on your 1099, you'll need to go back through your exchange history and download those transaction records. Some exchanges let you export your complete history as a CSV file, which can be really helpful. Then you'd need to calculate your gains/losses for those transactions or use one of the crypto tax services people have mentioned to help with that.

This matches what my CPA told me. He said the IRS doesn't expect Form 8949 to list thousands of trades, but rather to have reasonable summaries with backup documentation. He has clients who are day traders with stocks who do the same thing.

Do you think the $600 was worth the fee you paid to the tax pro? I'm wondering about the cost-benefit analysis. Also, now that you know about that credit, couldn't you just claim it yourself using software in future years?

Totally worth it - I paid $220 for the service, so I came out $380 ahead. And yes, now that I know about the credit, I can claim it myself going forward. I actually went back to software this year and made sure to look for that specific credit. I think seeing a pro once every few years as a "check-up" is a good strategy. Then you can self-file in between knowing you're doing it right. Tax laws also change pretty frequently, so it's good to get a professional review periodically.

Be careful with "free" filing! I tried that last year and as soon as I needed to file in two states they hit me with charges. Read the fine print - most of them only include ONE state for free.