If we go with partnership taxation, do my dad and I need to split everything 50/50 or can we have different percentages? Also, do we need to pay ourselves a salary or can we just take draws?

You can absolutely have different ownership percentages - it doesn't have to be 50/50. Your LLC operating agreement should specify the ownership percentages, and your K-1 forms will reflect those percentages for distributing profits and losses. For a partnership, you don't technically take "salaries" - you take draws, which aren't subject to withholding. However, you'll still pay self-employment taxes on your share of the profits regardless of whether you take draws or leave the money in the business. That's different from S-corps where you'd need to pay yourself a reasonable salary subject to payroll taxes.

For a new LLC filing as a partnership, you'll need to include Form 1065 Schedule B and check the box indicating it's an "initial return." You'll also need to select your tax year (usually calendar year for most small businesses). Make sure you've obtained an EIN before filing - you can't use your SSN for a partnership return.

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.

Thank you for the advice! I've already started working on my 2022 return and will file it this week. Is there any way to reduce the penalties since this is my first time making this mistake?

You can request penalty abatement under the IRS First Time Penalty Abatement policy if you haven't had any significant penalties in the past 3 tax years and have filed (or filed extensions for) all required returns. Call the IRS after you file and pay or set up a payment plan. Tell them you want to request "first-time penalty abatement" for reasonable cause. Explain that you misunderstood the withholding requirements with multiple jobs and that you've taken steps to correct it for the future. Many people get approved, especially for first-time mistakes.

You might want to update your W4 instead of just asking for extra withholding. If you use the IRS Tax Withholding Estimator online it'll tell you exactly how to fill it out for multiple jobs.

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.