Has anyone used FreeTaxUSA for business losses? TurboTax is crazy expensive and I've heard mixed things about their business support.

I went through almost the exact same situation last year with my freelance writing business. Lost about $3,500 in the first year after expenses for software subscriptions, professional development courses, and marketing that didn't pan out. The good news is that your business losses will definitely offset your other income on your tax return. Since you're a sole proprietor, you'll file Schedule C to report your business income (even if it's zero) and all those legitimate expenses you mentioned. The net loss will reduce your overall taxable income, which should result in a refund if you had taxes withheld from other income sources. A few things that helped me: - Keep detailed records of everything - receipts, bank statements, business purpose for each expense - Document that you're genuinely trying to make a profit (save emails about client outreach, business plans, etc.) - Consider opening a separate business bank account if you haven't already to keep expenses clearly separated TurboTax Self-Employed should handle your situation fine. It walked me through all the business expense categories and automatically calculated my loss. Just make sure you're honest about the business purpose of each expense and you should be good to go!

Anyone know if we can deduct unreimbursed expenses as a server against tip income? Like I buy my own server book, pens, and sometimes even help stock the bar when we run out of stuff during a shift. Would this help offset some of the allocated tip tax burden?

I went through this exact situation two years ago when I switched from a casual dining place to fine dining and suddenly had allocated tips on my W-2 for the first time. It was super confusing! The key thing I learned is that you absolutely should NOT just accept the allocated amount if it's higher than what you actually received. I kept detailed records of my tip-outs from the pool system (our restaurant gave us weekly summaries), and my actual tips were about $1,200 less than what was in box 8. I reported my actual tip income on my tax return and kept all my documentation. Never had any issues with the IRS. The allocated tips are really just the employer's way of meeting IRS requirements when the restaurant's overall tip reporting looks low - it doesn't mean that's what you personally made. My advice: gather any tip distribution records you have from your employer, compare them to what's in box 8, and report your actual income. If there's a big difference, definitely ask your manager how they calculated the allocation - sometimes there are errors that can be fixed.

For house hackers: Don't forget to take the 199A Qualified Business Income deduction for your rental activity! It's a 20% deduction on your qualified business income from the rental portion. This applies on top of your depreciation deductions.

Great discussion everyone! Just want to add one more important consideration for house hackers dealing with HVAC depreciation - make sure you're properly documenting the "placed in service" date for your depreciation calculations. Since you mentioned the system died and was replaced, the depreciation clock starts ticking from when the new HVAC system was installed and operational, not when you paid for it or when the old one failed. This matters for the MACRS half-year convention calculations. Also, keep detailed records of the installation invoice showing the breakdown between equipment costs and labor. Sometimes contractors will itemize things like ductwork modifications separately, which might have different depreciation schedules than the main HVAC unit itself. The IRS loves documentation during audits, especially for rental property deductions! One last tip: Consider getting a cost segregation study done if you're planning to acquire more rental properties. It can help identify components that qualify for faster depreciation schedules beyond just the HVAC system.

I work in mortgage lending and we accept the IRS Wage and Income Transcript in place of W-2s ALL THE TIME. It's actually preferred because it comes directly from the IRS and we know it hasn't been altered. Just make sure when you download it that you get the official PDF version and not just the web view.

Also want to mention that if you're having trouble with the IRS online identity verification process (which can be tricky), you can request transcripts by mail using Form 4506-T. It takes longer (usually 5-10 business days) but it's a reliable backup option if the online system isn't working for you. Just make sure to check the box for "Wage and Income Transcript" on the form, not just "Tax Return Transcript" - they're different documents and your mortgage lender specifically needs the wage information. You can download Form 4506-T directly from the IRS website and mail it to the address listed in the instructions. Given that your mortgage broker is getting impatient, I'd try the online transcript option first since it's immediate, but it's good to know you have this backup if needed!

Just want to add - if you're worried about any potential issues, you can also check the Treasury Offset Program website directly to see if you have any debts that might affect your refund. They have a lookup tool where you can verify if there are any holds on your account. Better to know ahead of time than be surprised when you file!

Been there! Had the same worry last year. As long as your loans are truly in deferment and not default, you should be fine. But definitely double-check your loan status on studentaid.gov like others mentioned - sometimes the paperwork gets mixed up between servicers. Also worth noting that even if you're in deferment, any interest might still be accruing depending on your loan type, so keep an eye on that too!