9 Did your wife have to register her business officially before claiming those deductions? I'm wondering if my husband needs a business license or official DBA name before we can start claiming his equipment purchases.

22 No formal business registration was required for tax purposes, though she did get a business license because our city requires one. For the IRS, you don't necessarily need a formal business entity to be considered "in business" and claim deductions on Schedule C. What mattered more was showing evidence of actually being in business - having clients, advertising services, maintaining business records, etc. The IRS looks for a profit motive and genuine business activity. Your husband should document when he transitions from just learning to actually seeking clients, even if it's just a few at first while still apprenticing.

19 I'm not the OP but I've been wondering about this too. Does forming an LLC actually help with tax deductions or is it mainly for liability protection? Is it worth the filing fees if you're just starting out?

12 How do you qualify for this First Time Penalty Abatement thing? Is it automatic or do you have to specifically request it?

3 You need to specifically request First Time Penalty Abatement - it's not automatic. The basic qualifications are: you haven't had any significant penalties in the 3 years before the tax year you're requesting abatement for, you've filed all currently required returns (or filed extensions), and you've paid or arranged to pay any tax due. You can request it by calling the IRS after filing all your returns, or your tax professional can help you submit the request. In my case, they removed about $4,300 in failure-to-file and failure-to-pay penalties, though I still had to pay the interest. Definitely worth asking for!

9 I filed 3 years of back taxes myself last year. It's definitely doable if you're organized and your situation isn't super complicated. The hardest part was getting all the right documents together. For the actual filing, I used FreeTaxUSA's prior year returns - they're only $15 per state return (federal is free) even for old years, much cheaper than TurboTax. Just make sure you're using the forms for the correct tax years and be meticulous about documentation, especially for self-employment income. Allow yourself plenty of time - each return took me about 3-4 hours.

In my experience, Fidelity has the quickest online process for solo 401ks. I was able to complete everything in about 30 minutes online last year. Vanguard required some paperwork to be mailed in which obviously wouldn't work for your deadline tonight.

This is actually not correct and could cause someone to miss the deadline. For a solo 401k, both adoption of the plan AND establishment of the account need to happen by December 31st. The funding can wait until the tax filing deadline, but the account itself must exist before the year ends. The confusion might be with SEP IRAs, which can be established up until the tax filing deadline. Solo 401ks have stricter timing requirements.

Oh shoot, you're right! I was mixing up SEP IRA rules with solo 401k rules. Thanks for the correction - definitely don't want to give anyone bad advice when it comes to retirement account deadlines.

Do you know if Cash App Tax has import features? I've heard mixed things but thinking about trying it this year.

Cash App Tax does have some import capabilities, but not as extensive as TurboTax. Last I checked, they could import W-2s by taking a picture, and they can import some 1099s from major brokerages like Robinhood and a few others. The coverage isn't nearly as comprehensive as TurboTax though, which can connect to hundreds of financial institutions. If you have accounts at smaller or less common brokerages, you might still need to enter things manually with Cash App Tax.

The free versions often miss deductions though. My cousin works for H&R Block and says they train them to upsell because the free version is designed to be incomplete.

So would selling stocks or crypto with capital gains trigger this? I did make about $3k in stock gains last year that I paid taxes on when I filed, but I didn't think that would trigger getting a 1040-ES for the next year.

Yes, capital gains from stocks or crypto could definitely trigger this if you ended up owing taxes when you filed. The $3k in stock gains without tax withholding would create a tax liability, and if your total tax due when filing was over $1,000, that would typically trigger the 1040-ES forms for the following year. The IRS essentially is saying "we noticed you had income without withholding last year, so we expect you might have similar income this year - please make estimated payments quarterly instead of waiting until tax time." It's their way of making sure you're paying taxes throughout the year on income that doesn't have automatic withholding like a W-2 job would.

If your tax situation is going to be significantly different this year (like you won't have the extra income that triggered it), you can technically ignore them. BUT - if you end up owing more than $1,000 when you file next year, you could face underpayment penalties. The safe approach is to either make the quarterly payments OR increase your withholding at your regular job to cover any expected tax. The IRS doesn't care how you pay throughout the year, just that you do.