Has anyone here actually filed separately and found it beneficial? My accountant keeps insisting joint is always better but I'm not convinced.

For your income levels ($160K and $155K), filing jointly is most likely going to be your best bet. With similar incomes, you won't hit the marriage penalty that affects couples where one spouse earns significantly more than the other. The math usually works out like this: joint filing gives you a higher standard deduction ($27,700 for 2023 vs $13,850 each filing separately), and you'll benefit from the more favorable tax brackets. Without kids or significant itemized deductions, you're looking at probably $2,000-4,000 in tax savings by filing jointly. The main exceptions where separate might be better: - If either of you has federal student loans on income-driven repayment (could lower monthly payments) - Significant medical expenses over 7.5% of your individual income - One spouse has tax debt/issues you don't want to be liable for Since you just got married in September, this is also a good time to update your W-4s with your employers to adjust withholding for next year based on your new filing status. Congrats on the marriage, and welcome to the world of joint tax planning!

Don't forget that depending on the value of the farmland, Nebraska might also have had estate taxes that would have been due upon your uncle's death. This is separate from the income/capital gains taxes you'll pay when selling. Did you have to file an estate tax return?

Are you planning to reinvest in other real estate? You might want to look into a 1031 exchange to defer the taxes if you're going to buy different investment property with the proceeds.

Has anyone actually calculated how much the student loan payment savings is compared to the tax hit? When my husband and I were in this situation, we found filing jointly saved us $3,200 in taxes, while filing separately only reduced student loan payments by about $1,800 annually. The math didn't work out for separate filing in our case.

Thanks everyone for the detailed responses! This is exactly the kind of insight I was hoping for. Based on what I'm reading, it sounds like I really need to run the numbers both ways before deciding. The student loan angle is particularly helpful since that wasn't something I had fully considered. A few follow-up questions: Since we bought our house in November, would the mortgage interest deduction be significant enough to tip the scales toward joint filing? We put down 10% so we're paying PMI too. Also, for my side gig income, I'm assuming I'd need to pay quarterly estimated taxes regardless of filing status - does that calculation change much between joint vs separate? I'm definitely going to try running both scenarios through tax software before making the final call. The state tax implications Nia mentioned are also something I need to research for Illinois specifically. Really appreciate everyone sharing their real experiences with this decision!

If you do end up needing to contact the IRS about this, you should know they won't do anything until after February 15th for missing W-2s. I tried calling earlier than that last year and they just told me to wait and contact my employer first.

Just wanted to add another perspective here - if your employer is generally reliable but just running behind, you might also want to check if they switched payroll companies recently. I had this exact situation two years ago where my W-2 was delayed because my company had just moved to a new payroll provider and there were some technical issues with generating the forms. In my case, I spoke directly with our office manager (we're a small company too) and she explained the delay and gave me a specific date when the W-2s would be ready. Having that timeline helped me plan my filing strategy. Also worth noting - if you do end up using Form 4852 or any substitute method, make sure to keep really detailed records of everything. Save your final paystub, any emails with your employer about the missing W-2, and documentation of when you contacted them. This will be helpful if the IRS ever has questions about your filing. The tax deadline is still a ways off, so you have time to work through this properly. Don't panic - this happens to more people than you'd think!

Just want to add something about the California thing you mentioned - some states have different e-filing schedules than the federal system. California does sometimes accept certain e-filings when the federal system is down for maintenance, but that's for state returns only, not federal. So while you might be able to e-file a CA state return during this period, it doesn't change anything about federal filing capabilities.

As someone who's been through this exact situation, I can confirm what everyone else is saying - that EA is definitely using pressure tactics. The IRS e-filing shutdown is routine maintenance that happens every year and has zero impact on regular 2024 tax filings. I made the mistake of rushing into hiring a tax preparer last year because of similar "urgent deadline" claims, and it cost me both money and quality service. Take your time to find someone reputable who doesn't resort to scare tactics. The fact that they're pushing you to sign "ASAP" over something that doesn't even affect your filing timeline is a huge red flag. A good tax professional would explain the actual deadlines clearly and let you make an informed decision without artificial pressure.