One thing nobody's mentioned yet - your local Low Income Taxpayer Clinic might be able to help for free. I used one when I owed $19k and had a similar spouse situation. They helped me get my OIC accepted without needing my ex's info. Google "LITC" plus your city name. They're funded by the IRS but operate independently to help people navigate tax issues. Mine helped me prepare all the documentation to prove financial separation and even represented me when the IRS had follow-up questions.

I went through almost the exact same situation last year - $29k debt, separated spouse who refused to cooperate, filing separately for years. Here's what actually worked for me: The IRS has a specific procedure for "uncooperative spouse" situations in OIC cases. You'll need to file Form 433-A marking "married" but include a detailed explanation letter stating your spouse refuses to provide information despite good faith efforts. Document EVERYTHING - send your spouse a certified letter requesting the information, keep the returned receipt when they don't respond. Include screenshots of texts where they refuse, witness statements if applicable. The IRS wants to see you made legitimate attempts. For the income question about your spouse, write "Spouse claims $0 income but has not provided verification. Applicant unable to obtain spouse's cooperation despite documented attempts." Don't guess or estimate - just state the facts. I also included 8 months of documentation showing our separate households (different addresses on all bills, leases, bank statements). The key is proving you maintain completely separate financial lives. My OIC was approved after some back-and-forth questions, and I paid about 25% of what I owed. The process took about 8 months total, but it was worth every day of stress. Don't give up - the IRS deals with this situation more often than you'd think.

You know what's interesting about this situation? The IRS actually has a right to hold your current refund against prior year liabilities. But what if you don't actually owe anything for those prior years? What if you were due refunds? You might be thinking "I don't need to file because I'd get money back" but there's a 3-year statute of limitations on claiming refunds. So you might want to calculate if you're actually due money from those unfiled years before they expire. The IRS won't remind you to claim your refunds before they expire, will they?

I went through this exact nightmare in 2022. The IRS held my $4,800 refund for 11 months while I scrambled to file 2019, 2020, and 2021 returns. Here's what I learned: First, prioritize getting your transcript immediately - it shows exactly which years are flagged and what hold codes are active. Second, file those missing returns electronically if possible, but don't stress if you have to paper file - both work, electronic is just faster for processing. Third, once you file the back returns, call the Practitioner Priority Line (855-821-0944) and ask them to manually review your account for hold release. I found this line had shorter wait times than the general taxpayer line. The agent was able to see my filed returns in the system and expedited the refund release. Total timeline from filing my last missing return to receiving my refund was 8 weeks. Stay persistent and document everything!

Has anyone used the IRS Tax Withholding Estimator? I tried it last year but my refund was still over $900 which seems way off from the "zero" it predicted.

The psychological aspect is huge here! I think a lot of people don't realize they're essentially giving the government a zero-interest loan when they overwithhold. But honestly, as someone who's terrible at saving money, I kind of appreciate getting that forced "bonus" each spring even though I know it's not optimal financially. What really helped me was using the IRS withholding calculator mid-year after I got my tax refund. I adjusted my W-4 to claim one additional allowance and ended up with only a $200 refund the next year instead of $1,500. That extra $100+ per month in my paychecks was way more useful than waiting for the lump sum. The key is being honest about your financial discipline. If you're someone who would just spend the extra monthly income on random stuff, maybe the forced savings of overwithholding isn't such a bad thing. But if you're disciplined enough to save or invest that extra money, definitely adjust your withholding!

Has anyone used the cost segregation strategy for rental property renovations? I heard you can depreciate some components much faster than 27.5 years. My accountant mentioned it might be worth looking into for my fourplex renovation but wanted to charge me $3000 for a study.

One thing to keep in mind is that if you're planning to hold this rental property long-term, depreciation is almost always the better choice over trying to claim repairs. Even if some of your $23,000 in costs could arguably be classified as repairs, the IRS tends to be pretty strict about what qualifies - especially for extensive work like kitchen and bathroom remodels. Since you mentioned using a property management company and having good documentation, you're already ahead of the game. Make sure to separate your costs by category (appliances, flooring, fixtures, etc.) because as others mentioned, some items may qualify for accelerated depreciation schedules. Also consider that you're required to take depreciation whether you claim it or not - the IRS will assume you took it when you sell, so you might as well get the tax benefit now rather than miss out on deductions and still face recapture later.

Thanks for all the helpful responses everyone! As someone who just started freelancing this year, this thread has been incredibly valuable. I was definitely overthinking the 1040-ES requirement - it sounds like I can just use the IRS Direct Pay system without worrying about submitting any forms. One follow-up question: If I'm using the safe harbor method (paying 100% of last year's tax liability), do I still need to use the 1040-ES worksheet to calculate my payments, or can I just take last year's total tax and divide by 4? My tax situation is pretty straightforward - just freelance income with standard business expenses. Also, does anyone know if there's a minimum income threshold where estimated payments become required? I've seen conflicting info about whether you need to pay if you'll owe less than $1,000.

Great question! I went through this same confusion when I started freelancing. The 1040-ES form is just a worksheet - you don't actually "file" it with the IRS. It's designed to help you calculate how much to pay each quarter. Here's what I learned: You can absolutely make your quarterly payments online without any paperwork. I use IRS Direct Pay (irs.gov/payments/direct-pay) - it's free, secure, and you just need your SSN and bank account info. When you make the payment, you'll select "Form 1040ES" as the form type and choose which quarter you're paying for. The key is keeping good records. Save your confirmation numbers and consider setting up an online account with the IRS so you can track your payment history. I keep a simple note in my phone with the confirmation numbers and dates - that's all the "filing" you really need for quarterly payments. Don't stress about not having a printer or avoiding tax prep services for this. The online payment system is actually much more convenient than mailing vouchers anyway!