I'm actually dealing with a similar situation right now! Just wanted to add that if you do decide to go ahead with the second job, make sure to keep really good records of all your expenses related to it - things like gas for commuting, work clothes if the retail job requires specific uniforms, etc. These can sometimes be deductible and help offset some of the additional tax burden. Also, since you mentioned credit card debt from your wedding, you might want to look into whether any of the interest is deductible (probably not for personal credit cards, but worth checking). The extra income from the second job could also help you qualify for better debt consolidation rates if that's something you're considering. One last thing - retail jobs during tax season (which you'd be starting soon) can sometimes lead to opportunities to learn about tax prep services, which could be another potential income stream down the road if you find you're good with numbers. Just a thought! Good luck with whatever you decide.

One thing I haven't seen mentioned yet is the timing aspect of starting your second job. Since we're already into 2025, you'll want to be extra careful about your withholding calculations because you'll have fewer pay periods to spread the additional tax burden across. I'd strongly recommend using the IRS Tax Withholding Estimator (irs.gov/W4App) rather than just the paper worksheet, since it can account for the partial year of second job income. When you input your information, make sure to include what you've already earned and had withheld so far this year from your main job. Also, consider this: at $58k + potential $12k from the retail job, you're looking at about $70k total income. That keeps you comfortably in the 22% bracket for 2025 (which doesn't kick in until around $47k for single filers). The real benefit is that extra $1000/month could knock out your credit card debt much faster, saving you tons in interest charges that far outweigh any additional tax burden. One practical tip: ask your retail employer about their payroll schedule. If they pay weekly while your main job pays bi-weekly, it might actually help smooth out your cash flow for debt payments!

I'm a real estate agent who works with a lot of self-employed buyers, and I can tell you that your proactive approach is exactly what sets successful transactions apart from the ones that fall through due to documentation issues. One thing I always tell my self-employed clients is to communicate with your real estate agent about this timeline too. If your agent knows you're waiting on tax transcripts, they can help manage expectations with the seller and potentially negotiate a longer financing contingency period if needed. Most sellers are reasonable about legitimate financing requirements, especially in today's market. Also, consider asking your lender for a timeline checklist of exactly when they'll need each document. This helps you coordinate not just the transcript timing, but also things like bank statements, profit & loss statements, and any other self-employment documentation they might require. Having everything ready in sequence prevents last-minute scrambles. Since you're buying in a competitive market where timing matters, you might also want to ask your lender about getting a stronger pre-approval letter that specifically mentions your tax documentation timeline. Something like "subject to receipt of 2024 tax transcripts" shows sellers that you're organized and have a clear path to closing, which can make your offer more attractive than other buyers who seem less prepared. The 8-week buffer you have should work perfectly with proper planning. Good luck with your purchase!

I'm actually a tax professional who specializes in helping self-employed clients with mortgage documentation, and I want to add a few points that might help streamline your process. First, when you file electronically, make sure to use the same bank account for your tax payment that you'll be using for your mortgage down payment and closing costs. Lenders often want to see consistency in your financial accounts, and having your tax payment come from a different account can raise questions that slow down underwriting. Second, consider filing a complete and accurate return even if you're missing a 1099 or two - you can always amend later if needed. The key is getting your return processed and your transcript available on schedule. Just make sure to keep detailed records of any missing documentation. One more tip: if you have quarterly estimated payments for 2024, make sure those show up correctly on your Account Transcript. Sometimes there's a lag between when you make estimated payments and when they appear on transcripts, which can confuse lenders who are trying to calculate your total tax liability. Your timeline looks solid, and the fact that you're thinking about this now puts you way ahead of most self-employed homebuyers. The January filing strategy everyone mentioned is definitely your best bet for getting those transcripts quickly.

Has anyone faced an audit for not reporting small gig income? I made like $200 on DoorDash last year and just didn't bother reporting it... now I'm worried.

I went through this exact same situation last year with about $400 in combined earnings from DoorDash and Grubhub. What worked for me in TaxAct was going to the "Business Income" section and selecting "I didn't receive a 1099-NEC" when prompted. You'll enter your total earnings as business income on Schedule C. For the payer information that TaxAct asks for, you can just put "DoorDash" and "UberEats" as separate business income sources and use your own SSN as the tax ID since you're operating as a sole proprietor. The key thing is to gather your own records - check your bank deposits, the payment history in both apps, and any email confirmations you received. The IRS accepts your own documentation when you don't have a 1099. Even though your amount is small, you'll still owe a bit of self-employment tax (about 15.3% of your net earnings after expenses), but it's usually not much on $350. And definitely track any car expenses you had - even without perfect mileage records, you can often reconstruct a reasonable estimate from your delivery history in the apps.

Has anyone actually gone through an IRS audit with an S Corp home office deduction including depreciation? Curious what documentation they asked for and how detailed the review was?

This is such a comprehensive discussion! As someone who went through a similar S Corp home office depreciation headache last year, I wanted to add one more consideration that nearly tripped me up. Make sure you're properly coordinating the depreciation method between your personal and S Corp books. I was using MACRS 39-year straight line for the business portion on my personal return, but my S Corp was trying to reimburse me based on a different calculation my bookkeeper had set up. The IRS expects consistency - the depreciation your S Corp reimburses you for should match exactly what you're claiming as a deduction on Schedule E. Also, don't forget about the Section 280A limitations! Even with an accountable plan, you can't deduct home office expenses (including depreciation) that exceed the gross income from the business use of your home. This rarely comes up, but if your S Corp is having a tough year, it could potentially limit your depreciation deduction even if the reimbursement goes through properly. One last tip: consider setting up your accountable plan to reimburse monthly rather than annually. It makes the cash flow smoother and creates a better paper trail for documentation purposes. My CPA said it also makes audits less likely to raise red flags since the transactions look more like regular business operations rather than year-end tax planning moves.

I'm not sure if anyone mentioned this, but most tax software has a specific "part-year resident" wizard or interview section. For example, in TurboTax, there's a separate section for "I lived in more than one state." Have you specifically completed that section? Also, double-check your W-2s. Sometimes employers mess up and put the wrong state code on your W-2, which can cause exactly the issue you're describing. My company once put CA on my W-2 even though I had moved to OR, and it caused a similar double-taxation problem.

This is a classic multi-state tax issue that trips up a lot of people! The key thing to understand is that you should NOT be paying full income tax to both states - that's definitely wrong. Here's what's likely happening: your tax software is treating you as a full-year resident of both states instead of a part-year resident. This causes it to calculate taxes on your entire annual income for both states, which is exactly what you're seeing. To fix this, you need to: 1. Make sure you've selected "part-year resident" (not just "resident") for both NY and VA 2. Enter your exact move date (July 1st, 2024) 3. Verify that your NY income is only what you earned Jan-June while living in NY (~$52k) 4. Verify that your VA income is only what you earned July-Dec while living in VA (~$19k) The taxable income amounts you're seeing ($61k for NY, $58k for VA) suggest the software is applying deductions incorrectly or double-counting income. Once you fix the residency settings, those numbers should drop dramatically. Also, just to confirm - you mentioned having separate W-2s from each employer. Make sure when you enter each W-2, you're telling the software which state that job was performed in. This helps the software properly allocate the income. Good luck! This should result in a much better outcome once sorted out properly.