Florida requires C corporations that are doing business in Florida to file Form F-1120 (Florida Corporate Income Tax Return) regardless of whether they have any tax liability. Even if your corporation falls below the income threshold where you'd owe tax, you typically still need to file the return. There is an exception for corporations not doing business in Florida and corporations that have no income reportable to Florida. So it depends on where your C corporation is operating and generating income. Florida does have filing exemptions for certain entities like S corporations and certain non-profits, but standard C corporations generally need to file.

Does H&R Block handle the capital gains calculation correctly? My situation is complicated because some of my RSUs vested early in the year and then I sold them months later when the price had changed quite a bit. I need to make sure I'm reporting both the initial income and the capital gains/losses correctly.

Yes, H&R Block handles the capital gains calculation correctly. It separates the initial income recognition (which appears on your W-2) from any subsequent capital gains or losses that occur between vesting and selling. When you enter your stock sales, you'll provide both the sale price and the cost basis (which is the fair market value on the vesting date). The software then correctly calculates only the difference as capital gains/losses. It's much more straightforward than TurboTax, especially for situations where there's a significant time gap between vesting and selling with price changes.

Form 3922 is for ESPP (Employee Stock Purchase Plans), not RSUs. For RSUs, employers typically provide a summary statement but not a specific IRS form. Most just include it on your W-2 and provide supplemental information.

Thanks for this clarification! So if I understand correctly: I should definitely file Schedule C with my business expenses to reduce my self-employment tax, but that's completely separate from deciding between itemized vs. standard deduction? And since my total income is only around $32,500, the standard deduction ($13,850) is probably better unless I have some major itemized deductions?

Yes, that's exactly right! File Schedule C to report your 1099 income and expenses (which reduces or eliminates self-employment tax on that income). And yes, at your income level, you'll almost certainly want to take the standard deduction unless you have extraordinary itemized deductions like major medical expenses, huge charitable contributions, or large mortgage interest payments. For most people in your situation, itemized deductions don't exceed the $13,850 standard deduction.

Just be careful with the home office deduction - it has to be a space EXCLUSIVELY used for business. If you sometimes use that desk/room for anything personal, it doesn't qualify. I got audited over this once.

Thank you for this insight. I hadn't considered doing just a consultation. Would that one hour really be enough to catch potential issues across multiple tax years including the business transition?

A one-hour consultation won't be comprehensive enough to catch everything across multiple years, but it would be enough time to identify major red flags in your approach and give you guidance on the areas where software typically fails for business returns. If you're going the DIY route, I'd actually recommend two consultations - one before you start to get a strategic approach, and one review after you've prepared the returns but before filing. The key is finding someone experienced with both the sole proprietor to LLC transition and back tax situations.

The Fresh Start program isn't actually a specific program you apply for - it's a collection of different IRS initiatives that make it easier to resolve tax debt. The main components are expanded installment agreements, offers in compromise with more flexible terms, and tax lien procedures. For OP's situation with unfiled returns, the most relevant part would be penalty abatement options after filing the back returns. First-time penalty abatement is available to many taxpayers who haven't had previous issues.

That's really interesting! I do have a small side business doing web design that brought in about $12,000 last year. Would I qualify for this SEP IRA option? And can I open one if I also have access to my employer's 401k from my main job?

Yes, you absolutely can set up a SEP IRA for your self-employment income, even while having access to an employer 401k! The two are independent of each other. The calculation gets a bit tricky though - it's not simply 25% of your gross $12,000. For self-employment income, you first need to deduct the self-employment tax deduction, then calculate 25% of that reduced amount. With $12,000 in net business income, you could probably contribute around $2,200-2,500 to a SEP IRA. That would directly reduce your taxable income for 2023 if you establish and fund the account before filing your taxes. Many brokerages like Vanguard, Fidelity, or Schwab offer SEP IRAs that you can open online pretty quickly.

The work-related educational expenses deduction was suspended until 2025, so that's unfortunately not an option for 2023 taxes. The moving expense deduction is indeed only for active duty military now too. But good call on the self-employed health insurance premiums! If OP has self-employment income as mentioned above, they might be able to deduct health insurance premiums paid.