One thing nobody's mentioned yet - make sure you understand the timing requirements for S-Corp election. You need to file Form 2553 within 2 months and 15 days of the beginning of the tax year you want the election to take effect. If you miss that window, you're generally stuck waiting until next year (though there are some late election relief options). Also, keep in mind that an S-Corp must have a calendar year end (Dec 31). And once you start having the company pay your LLC, you'll need to keep clean books, potentially open a separate business bank account, and make sure you're segregating business and personal expenses.

Has anyone considered the other costs involved with S-Corps? I'm looking at this same transition and discovered: 1. State franchise tax in my state (CA) is $800 minimum per year just to have an LLC 2. I need a registered agent ($100-300/yr) 3. Payroll service fees ($40-60/month) 4. Accountant fees for S-Corp tax return (~$1000+) 5. Bookkeeping software ($25+/month) Plus the hassle of running payroll, maintaining corporate minutes, etc. Seems like you need to be making good money for this to be worth it.

4 Something important nobody's mentioned yet - check if your parents are claiming you as a dependent on their US taxes! If they are, you can't claim education credits yourself. They would have to claim them based on any expenses they actually paid for your education. I learned this the hard way last year when both my parents and I tried claiming my education expenses (they paid for my housing, I paid for books and materials), and it caused a whole mess with the IRS that took months to sort out.

10 Quick tip about documenting those second-hand book purchases without receipts: take photos of the books with the course number and your name visible, screenshots of any electronic transfers you made to pay for them, and keep a spreadsheet with dates, amounts, and course information. Also save your course syllabi that show these materials were required. I did this for my study abroad in Spain, and it was enough documentation when I claimed the Lifetime Learning Credit. I got about $200 back, which wasn't huge but definitely helped!

Has anyone mentioned state taxes yet? If your state has income tax, you're probably behind on those too, and each state has different penalties and payment options. Don't forget to address both federal AND state when you're getting caught up!

Make sure when you file that you look into business deductions carefully. As self-employed, you can deduct legitimate business expenses like home office, equipment, software, professional development, travel for business, etc. This could substantially reduce what you owe. Might be worth consulting with a tax professional who specializes in self-employment taxes before filing.

Something nobody's mentioned is that you should make sure you enter the 401k distribution correctly in your tax software. When I did this last year, TurboTax initially calculated that I owed the 10% penalty because I didn't check the right exemption box. Double check that you've properly indicated any applicable exceptions to the penalty. Also, while the 20% withholding will be counted toward your total tax, remember the distribution itself will be added to your income, which could potentially push you into a higher tax bracket or reduce some of your credits. Every situation is different - it might be worth consulting with a tax professional given your specific circumstances.

Were you able to document the foundation repairs as a qualified hardship? I had to take a 401k withdrawal for medical expenses last year and was able to avoid the 10% penalty entirely by showing that the expenses exceeded 7.5% of my adjusted gross income. The financial institution still withheld the 20% for taxes, but I got that back when I filed because my actual tax rate was lower. Just make sure you keep ALL receipts and documentation from the foundation repair. The IRS can request proof up to 3 years after you file.

Something nobody mentioned yet - check if TurboTax actually DID generate the form but just didn't tell you to mail it. In the tax return PDF that TurboTax generated, search for "8453" and see if the form is included somewhere in there. Sometimes TurboTax generates forms but doesn't make it clear what you're supposed to do with them. I've had situations where I found forms buried in my final tax PDF that I didn't even know existed!

The rule of thumb I've been told by my accountant is: if you don't have a 1099-B from your crypto exchange, but you DO have transactions that would typically be reported on a 1099-B, then you should submit Form 8453 with a statement explaining your situation. Even though it's months later, I would still file it. Write a cover letter explaining that TurboTax didn't properly instruct you to file Form 8453, include a printout of your detailed transactions (not just the summary), and mail it to the IRS. Better to voluntarily provide more information than have them come asking for it later!