Just my experience, but I deducted my hearing aids last year as a medical expense along with some dental work and surgery costs. The combined amount got me over the 7.5% threshold. When you file, make sure you keep all receipts and documentation from your audiologist about the medical necessity. I also got a letter from my doctor explaining why I needed them, which helped support the deduction.

It's not too complicated to itemize, especially if you have substantial medical expenses like hearing aids. You'll use Schedule A instead of taking the standard deduction. The key is making sure your total itemized deductions (medical expenses over 7.5% of AGI, state/local taxes, mortgage interest, charitable donations) exceed the standard deduction amount to make it worthwhile. For 2024, the standard deduction is $14,600 for single filers and $29,200 for married filing jointly. If your hearing aids plus other medical expenses get you over that 7.5% AGI threshold and your total itemized deductions beat the standard deduction, then it's worth doing. Most tax software will automatically calculate both scenarios and tell you which saves you more money.

just wanted to add that TurboTax will actually calculate your return both ways (jointly and separately) and tell you which one saves you more money! I use it every year and it always compares them automatically. super easy.

I went through this exact same dilemma when I got married! One thing that really helped me was creating a simple spreadsheet to track all our deductions and credits under both scenarios. Since you mentioned using TurboTax, definitely take advantage of their comparison feature, but also consider these factors: if either of you has high medical expenses, significant charitable donations, or if one spouse has much higher income than the other. The two-state situation actually isn't as complicated as it seems - most tax software handles it pretty smoothly regardless of filing status. My advice? Run the numbers both ways in TurboTax first, then if you're still unsure or the difference is small, consider getting a second opinion from a tax professional or one of those analysis tools others mentioned. Better to spend a little time now than leave money on the table!

I'm surprised nobody mentioned that you need to be careful with this if you're taking the simplified home office deduction of $5 per sq ft! If you go that route you cant deduct actual expenses like rent or utilities separately. You have to pick one method or the other.

I went through this exact same situation when I started freelancing! The key thing to remember is that you need to have an actual expense to deduct. Since your boyfriend pays the rent and you don't reimburse him, you technically don't have a deductible rent expense right now. However, there are a few ways to handle this: You could start paying your boyfriend for your portion of the rent (get a simple written agreement for documentation), or you could take over paying for other home expenses like utilities, internet, or maintenance that you can then deduct proportionally for your office space. Another thing to consider - if you're using 25% of the apartment exclusively for work, you might want to calculate both methods to see which gives you a better deduction. The actual expense method might be worth more than the simplified $5/sq ft method depending on your total housing costs, but the simplified method is much easier to track and document. Make sure whatever arrangement you set up, you keep good records. The IRS loves documentation for home office deductions!

Does anyone know if there's a statute of limitations on unfiled FBARs? I'm in a similar situation but it's for 2020, not 2022.

I went through something very similar in 2021 with a property transaction in Italy. The key thing I learned is that the IRS really does look favorably on voluntary disclosure before they contact you. I filed my delinquent FBAR about 8 months late and received no penalties. One important detail for your situation: make sure you report the correct maximum balance for 2022. Since you received that $85K deposit in September, your maximum balance would include that amount even though the full transaction didn't complete until 2023. The FBAR requires reporting the highest balance at any point during the year, not just year-end balances. Also, don't stress too much about the timing of filing your 2023 FBAR alongside your tax return in April. The FBAR deadline is actually April 15th with an automatic extension to October 15th (no need to request it), so you have plenty of time to get both years filed properly.

Does anyone know if you can have multiple SMLLCs? Im thinking about starting a second business but keeping it separate from my first one. Would I report both on the same Schedule C or have multiple Schedule Cs?

Great question! I went through this exact same confusion last year with my SMLLC. Here's what I learned after consulting with a tax professional: For issuing the 1099-NEC: Use your LLC's information (LLC name, EIN, and LLC address) as the payer. Even though it's a disregarded entity for income tax purposes, the LLC is still the legal entity that made the payment to your contractor. For your mixed 1099s: You're absolutely right to report both exactly as issued on your tax return. The one with your SSN goes on Schedule C as normal business income, and the one with your LLC's EIN also goes on Schedule C (same schedule). TurboTax handles this well - just make sure when you enter the LLC's 1099, you indicate it's for the same business activity. One tip that saved me headaches: Keep really good records showing which payments came through which entity. It helps during tax prep and if you ever get questions later. Don't stress too much about being late on the 1099-NEC - as long as you get it filed soon, the penalties aren't usually too severe for first-time issues. The important thing is getting it right going forward!