1 I actually don't have an accountant yet - part of why I'm in this mess! Been trying to handle everything myself to save money in the first year, but clearly that's not working out so well. Do accountants typically take on new clients same-day when there's a deadline?

3 Many accountants do offer same-day extension filing for new clients, especially during tax season. It's a common way they begin relationships with new business clients who are in a bind. A simple extension filing is low-risk for them and gives you both a chance to work together. I'd recommend calling a few local business accountants and explaining your situation. Be clear that you need the Form 7004 filed today and ask if they can help. Even if they can't take you on as a full client right away, many will handle just the extension filing to help you meet the deadline.

1 Oh crap, I didn't realize that! I haven't calculated what I might owe yet. Is there a quick way to estimate this, or do I need to basically do all the tax calculations anyway?

14 You don't need to do the complete calculations, but you should make a reasonable estimate based on your business income and expenses for the year. A safe approach is to look at what you paid last year (if you were in business) and pay at least that amount. If this is your first year, calculate your rough profit and multiply by the appropriate tax rate. If you're really unsure, it's generally better to overpay slightly and get a refund later than to underpay and face penalties. Even a good faith estimate shows the IRS you're trying to comply, which can help if you end up slightly short.

But Florida has higher property taxes and insurance costs, right? Did that eat up some of the tax savings?

Can new residents immediately contribute to 401ks? I thought there might be waiting periods or residency requirements for tax-advantaged accounts.

There are no residency requirements for 401k eligibility from a tax perspective - it's based on your employment status, not your citizenship or residency history. As soon as you're legally authorized to work in the US (with appropriate visa/work permit) and your employer offers a 401k plan, you can contribute. Some employer plans do have waiting periods before you're eligible (commonly 3-6 months), but that's a company policy issue, not a tax or legal requirement. Your employer may also have a vesting schedule for their matching contributions, but your personal contributions are always 100% vested. The key thing is having a Social Security Number or Tax ID Number, which you'll need anyway for employment.

This is really helpful. I think I might not qualify since the kids are primarily with their mom, but I'll double check the requirements. Do you know if there's any documentation I need to keep in case the IRS questions my filing status?

You should definitely keep records showing when your separation began - any legal separation documents, lease agreement for your apartment showing when you moved out, and anything documenting your custody arrangement. Also save records of all household expenses you paid (rent/mortgage, utilities, repairs, food, etc.) to prove you paid more than half the cost of keeping up a home if you try to claim Head of Household. If the kids are primarily with their mom, you probably won't qualify for HOH. But if she's willing, she could release the dependency exemption to you using Form 8332 (though she'd still claim HOH). This form specifically allows the custodial parent to release the child's exemption to the non-custodial parent.

The stimulus payments were years ago though? I don't think there have been any since 2021. Are you saying we can still claim them somehow if we didn't get the right amount back then?

Is it really 30%? That seems crazy high! Do you really need to set aside that much? I just started freelancing and haven't been saving nearly that amount...

The 30% is a safe estimate that covers federal income tax, state income tax (depending on your state), and self-employment tax (which is 15.3% alone). It's better to save too much than too little. Your actual rate will depend on your total income, deductions, credits, and state. If you're in a high-income bracket and a high-tax state, it could actually be higher than 30%. If you're in a lower bracket or a state with no income tax, you might need less. But starting with 30% is usually a good rule of thumb for most freelancers.

Nope, their classification doesn't affect yours. You're still an individual/sole proprietor regardless of how the entity paying you is structured. Their business structure only matters for their taxes, not yours.

That's a great suggestion I hadn't considered. My dad was always pretty diligent about filing on time before he got sick, so he probably would qualify. Do I need to file a specific form for this abatement request or just call and ask for it?

You don't need a specific form for First Time Penalty Abatement. The easiest approach is to call the IRS directly and make a verbal request. Make sure to specifically use the phrase "First Time Penalty Abatement" when speaking with the representative. If you prefer to request it in writing, you can submit a penalty abatement letter that clearly states you're requesting First Time Penalty Abatement. Include your father's name, SSN, the specific tax year (2019), and a statement confirming that he had a history of compliance for the three prior years. Attach a copy of the death certificate as well.

This is so true. My brother never filed his 2017 taxes and the IRS created a substitute return for him in 2022 that assessed over $12,000 in taxes because they only counted income and NONE of his deductions or credits. He would have actually been due a refund if he'd filed properly. Don't wait!