I actually haven't looked into the S-corp angle yet. How complicated was it to set that up? And does your accountant think the educational assistance program would work even for something like nursing school that leads to a different license?

Setting up the S-corp wasn't too complicated with my accountant's help - took about a month total. The key advantage is that the Section 127 educational assistance program doesn't have the same "current skills" requirement as Schedule C deductions. The program can cover any education, even if it leads to a new credential or license, as long as you set it up properly and follow the rules. My accountant confirmed it would work for nursing education. The $5,250 annual limit is the main restriction, so it wouldn't cover full-time tuition, but it's a tax-free benefit that could significantly reduce your out-of-pocket costs while staying completely above board with the IRS.

This is actually really smart. My sister went this route and had her entire nursing program paid for by working 24 hours/week at the hospital. She kept her weekend lash business going too. Much cleaner from a tax perspective!

Thanks for breaking this down! So for my situation with no kids, renting an apartment, but living in a high tax state (NY), it sounds like the SALT cap would be the biggest factor to consider? The guide I saw didn't mention how this interacts with Schedule C income.

The SALT cap would definitely be a significant factor for you living in NY. For your Schedule C photography income, the SALT cap interacts a bit differently than with your regular income. While your state/local income taxes are subject to the SALT cap, your business expenses on Schedule C remain fully deductible as business expenses. One thing many people miss is that self-employment taxes (the 15.3% for Social Security and Medicare) apply to your net Schedule C income regardless of SALT considerations. Make sure you're tracking all legitimate business expenses for your photography work to reduce that SE tax burden.

Most simplified guides completely overlook the AMT implications, which is a huge oversight for people with stock options. The AMT has been modified several times in recent tax legislation, with exemption amounts and phaseout thresholds changing. If you have stock options, especially incentive stock options (ISOs), you need specialized tax advice because the regular vs. AMT calculation can vary dramatically. Generic tax plan summaries almost never capture these nuances.

That's what I was worried about. I exercised some ISOs last year and the tax implications were completely different than what the general calculators showed. Guess I'll need to talk to my accountant about this specifically rather than relying on these guides. Thanks!

I asked my tax preparer about this last week! Amended returns for tax year 2021 would normally be due by April 18, 2023 (the standard 3-year amendment period). If you're in the disaster area, this deadline is also extended to October 16, 2023. So yes, you have until October to file that 2021 amended return!

Thank you so much for checking on this! That's a huge relief as I'm still gathering documentation for some expenses that were damaged in the flooding. Good to know I have until October to get everything together for the amendment.

It's automatic! If your primary residence or business is located in the federally declared disaster area, you don't need to file any extension forms. The IRS automatically provides the relief to anyone in the covered disaster areas. The system is set up to recognize your location based on your address on file with the IRS.

Thanks for this info! I had no idea the IRS could help with missing W2s or that employers had a deadline for sending them. My company is definitely past that February 15th deadline now so maybe that's why they're being so slow about it. I'll definitely try calling that number. Do you know if there's a way to check online whether my employer has already submitted my W2 info to the IRS? That would save me time on the phone if I could see it's already in their system.

Unfortunately there isn't an online way to check if your specific W2 has been filed with the IRS yet. The only way to get that information is by calling them directly. One thing you might try though is creating an account on the IRS website (if you don't already have one) at irs.gov/account. While it won't show your current year W2 info before you file, it will at least give you access to request a wage and income transcript from previous years, which can be helpful for reference.

This is the most important advice in the thread honestly. The extension is ONLY for filing paperwork, not for paying what you owe! I think a lot of people don't realize this.

Wait, I thought the special rule for charitable donations when taking the standard deduction expired after 2021? Is that still available for 2023?

You're absolutely right, and I apologize for my error. The special provision that allowed taxpayers to deduct charitable contributions while taking the standard deduction was temporary and has expired. For 2023, you would need to itemize deductions on Schedule A to claim charitable contributions. Thanks for the correction - it's important to have accurate information when making these last-minute tax decisions!

Good point! Most online platforms have a dropdown or option to select which tax year the contribution is for, but it's easy to miss. I always take a screenshot of the confirmation page showing the tax year just to be safe.

That's a smart approach with the screenshot! I've started doing something similar. When I make my contribution now, I actually call my financial institution afterward to verbally confirm they've recorded it for the correct tax year, then note the date, time and representative's name. It takes an extra few minutes but saves potential headaches later.