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Be careful with going directly to an IRS office. I made that mistake. They made me fill out a bunch of forms, which seemed helpful at the time, but then I got even MORE confused notices afterward. Your situation sounds like a classic case of incorrect income reporting. Someone (probably your former employer) submitted a 1099-K with your SSN attached to their account. The fact that Stripe won't help is unfortunately typical - they usually require the account owner to make any changes. Document EVERYTHING. Every call, email, letter. Keep copies of your employment termination paperwork. Get an official employment verification letter if possible. You might even need to file a Form 14039 (Identity Theft Affidavit) if your former employer doesn't fix this.
Thanks for this advice! I never thought about filing an identity theft form, but that makes sense if my info is being used on an account that isn't mine. Have you dealt with incorrect income reporting yourself? How long did it take to get resolved?
Yes, I had a similar issue when a company I briefly consulted for reported all their platform income under my SSN by mistake. It took about 5 months to fully resolve, which was frustrating but eventually worked out. The Identity Theft Affidavit is helpful because it flags your account in the IRS system and can help prevent collection activities while you're resolving the dispute. Just be clear in your explanation that this is a case of incorrect income reporting by a business, not someone stealing your identity for credit fraud.
Don't waste your time with H&R Block for something this complex. You need a CPA who specializes in tax controversy or a tax attorney. The IRS has a procedure called "substitute for return" where they create a tax return for you based on income reported under your SSN if they think you didn't file. They probably got a 1099-K from Stripe with your SSN and assumed that income was yours. Get a CP2000 transcript and wage/income transcript from your IRS online account. This will show exactly what was reported and by whom. Sometimes the business name will be listed and that might help confirm it's your former employer.
This is exactly what happened to me in 2023! Request those transcripts ASAP because they'll show the exact source of the reporting. In my case, it was a former business partner who kept using my SSN for company accounts after I left. Such a nightmare to fix.
One piece of advice from someone who's been in your situation - if you go with a CPA, make sure they specialize in multi-state returns and investment properties. I made the mistake of going with a general tax preparer last year after my California to Texas move, and they missed several deductions related to my rental property. If you decide to use tax software, set aside a full weekend to work through it. The multi-state portion takes longer than you'd expect, especially with rental income in the mix. And keep all your moving-related receipts - some might be deductible depending on your work situation.
Thank you for this advice! Did you find it difficult to verify if a CPA truly had expertise with multi-state returns? I'm worried about just taking someone's word for it and then finding out they weren't as experienced as they claimed.
That's a valid concern! I'd recommend asking potential CPAs specific questions about your situation before hiring them. Ask how many multi-state returns they handle annually and specifically about rental property scenarios similar to yours. An experienced CPA should be able to immediately discuss specific forms (Schedule E, part-year resident forms) and potential pitfalls without hesitation. Also, don't just go with someone who says "yes, I can do that" - ask them to explain HOW they would approach your specific situation. A truly experienced multi-state CPA will mention things like sourcing rules, reciprocity between states, and credit for taxes paid to another state. If they can't speak to these specifics, that's a red flag.
I'm going through literally the exact same thing (moved from NY to MA with a rental property in NY). I tried using TurboTax Premier and it was a nightmare - kept getting contradictory guidance about how to handle the rental depreciation with the state split. Finally broke down and hired a CPA in Massachusetts who had experience with NY properties. Cost me $475 but honestly worth every penny for the peace of mind. He found several deductions related to my move that I had no idea about. If you're not in a rush, you could try starting with tax software to see if you can handle it, knowing you can always bail and go to a professional if it gets too complicated. Just don't wait until April 14th to make that decision!
In my experience as a long-time 1099 contractor, the hotel deduction in this case is risky. Since you're primarily going to visit family, the IRS would likely consider this a personal trip. The fact that your parent company is there doesn't help unless you're actually conducting business with them in person. A better approach might be to look at coworking spaces in the area instead of the hotel. You could deduct the daily fee for the coworking space as a clear business expense since it's only being used for work, while staying with family. This creates a cleaner separation between personal and business expenses.
I hadn't thought about coworking spaces! That's a really smart alternative. Do you know if there are any specific documentation requirements for using coworking spaces as a business expense? And would that still work if I keep the hotel for personal comfort but also use a coworking space?
For coworking spaces, keep the receipts/invoices from the space and note the business activities performed there each day. Take photos of your workspace and save any digital check-ins. If you're producing deliverables while there, note that in your records. You could absolutely still keep the hotel for personal reasons while using a coworking space for business. This actually creates a much cleaner deduction situation because the coworking space has no personal use component - it's 100% business. The hotel would then be clearly personal and non-deductible, but your dedicated workspace would be fully deductible. This arrangement also makes it much harder for the IRS to question the business purpose since there's no mixing of personal and business use in the same space.
As someone who's been a 1099 contractor for 5+ years, I would strongly recommend against trying to deduct the hotel in this case. I tried something similar in 2021 and it triggered an audit. The IRS agent specifically cited the primary purpose test and disallowed my deduction since the primary purpose of my travel was personal. One thing no one has mentioned - have you considered checking if your company might have a corporate rate at any hotels in the area? My client company had a business rate at several hotels that was cheaper than regular rates, even though they didn't pay for my stay.
One thing nobody's mentioned yet - have you double checked your withholding on those W-2s? With 4 different jobs between you, it's possible that each employer is calculating withholding as if that's your only income, which would lead to significant underwithholding. You might need to submit new W-4 forms to each employer and select the "Multiple Jobs" option or specify an additional amount to withhold from each paycheck. This won't help for 2023, but could prevent the same surprise for 2024.
That's a good point I hadn't considered. I think each employer is definitely calculating as if that's our only income. How would I figure out what the right additional withholding amount should be for each job? Is there a calculator for that?
The IRS has a Tax Withholding Estimator tool on their website that's designed exactly for situations like yours with multiple jobs. It will walk you through entering info from all four W-2s and then recommend specific withholding amounts for each job. For a quick rule of thumb, take your total expected annual tax bill (probably around $44-45k based on your income) and subtract what you're currently having withheld. Then divide that shortage by the number of pay periods remaining in the year to determine how much additional withholding you need across all jobs. You can split that amount across all four jobs however makes sense for your cash flow.
Has anyone mentioned looking into any tax credits you might qualify for? The Child Tax Credit, American Opportunity Credit (for education expenses), or Saver's Credit could apply depending on your situation. Credits are even better than deductions since they directly reduce your tax bill dollar-for-dollar.
At their income level ($270k), they're probably phased out of most credits. The Saver's Credit phases out at $73k for married filing jointly, and the Child Tax Credit starts phasing out at $200k. Education credits have similar income limitations.
AaliyahAli
Has anyone claimed the Lifetime Learning Credit for online courses that aren't from a traditional college? I took some programming bootcamp classes that were about $7,000 and got a 1098-T, but I'm not sure if they qualify?
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Ellie Simpson
β’For Lifetime Learning Credit, the educational institution needs to be eligible to participate in federal student aid programs. Many coding bootcamps don't qualify because they aren't accredited in the right way. Check if your bootcamp has a Federal School Code and if they're on the Federal Student Aid Code List. If they gave you a legitimate 1098-T that's a good sign, but double-check their eligibility on the IRS website just to be sure!
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AaliyahAli
β’Thanks for that info. I just checked and my bootcamp does have a Federal School Code. I was confused because it's not a traditional 4-year college, but apparently they do qualify for federal aid programs. Guess I'll go ahead and claim it!
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Arjun Kurti
Quick tip that saved me last year: When using FreeTaxUSA for the Lifetime Learning Credit, make sure you enter the amounts from your 1098-T correctly. The software will ask about Box 1 (payments received) and Box 2 (amounts billed). My school only filled out Box 1 and left Box 2 empty, which confused me. Watch out for this! You should use the amount that represents what you actually paid during the tax year, regardless of which box it's in. Also remember that the Lifetime Learning Credit is 20% of your eligible expenses up to $10,000, so max credit is $2,000. But your income might reduce this - starts phasing out at $80,000 for single filers.
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RaΓΊl Mora
β’This Box 1 vs Box 2 thing tripped me up too! My school put stuff in both boxes and I had no idea which one to use. Does anyone know the difference?
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Arjun Kurti
β’Box 1 shows amounts the school actually received during the calendar year, while Box 2 shows amounts that were billed for qualified expenses during the year. The difference matters because of timing - sometimes you might pay in December for classes starting in January, or pay in January for classes that started the previous December. You generally want to claim the credit in the year you actually paid the expenses, which would align with Box 1. However, you should look at both boxes and understand what educational expenses they represent. If there's a big difference between them, you might need to figure out exactly when you made payments and what academic periods they were for.
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