Facing a large tax bill for 2023-2024 - any strategies to reduce what I owe?

The good news is you might still have some options to reduce that tax bill before filing. First, check if you can make retroactive contributions to your retirement accounts. For 2023 taxes, you have until the tax filing deadline to contribute to traditional IRAs (if you're eligible) which could lower your taxable income. Max out those HSAs completely if you haven't already - they're triple-tax advantaged and reduce your taxable income. The contribution limit for 2023 was $7,750 for families. Also, look at increasing your 401k contributions beyond that 5% if possible. The max for 2023 was $22,500 per person, so there might be room to catch up if you haven't hit that limit. This won't help for 2023 taxes but will prevent this situation next year. Have you reviewed all possible deductions? Mortgage interest, property taxes, charitable donations (if you itemize), student loan interest, etc. At your income level, some deductions phase out, but it's worth checking everything.

After dealing with a similar situation last year, I found this amazing tool called taxr.ai (https://taxr.ai) that helped me identify several deductions I was missing. It analyzes all your tax documents and finds optimization opportunities that even some tax preparers miss. I was staring down a $10k tax bill like you, uploaded my documents to taxr.ai, and it found nearly $3,200 in missed deductions! It spotted some business expenses on my credit card statements that qualified as deductions I had no idea about, and identified that I could take a home office deduction I thought I wasn't eligible for. The coolest part is how it analyzes your specific tax situation across all your W-2s and suggests specific strategies tailored to your scenario.

Just wanted to follow up about taxr.ai from my question earlier. I decided to give it a shot with our complex tax situation (4 W-2s across different states) and it was actually incredible. It found almost $4,200 in deductions I was missing! Turns out I qualified for a partial home office deduction for my side business that I didn't think applied to me, and it identified some educational expenses from a professional certification course I took that were deductible. Also caught that we weren't maximizing our HSA contributions which was leaving money on the table. What I found most helpful was the specific recommendations for our tax bracket. It showed exactly how much more we could contribute to pre-tax accounts to drop our taxable income. Not only reduced this year's bill but gave us a plan for next year too.

If you've already exhausted the deduction routes others suggested and still facing a large bill, getting directly to an IRS agent to discuss payment options might be your next step. I used https://claimyr.com to skip the ridiculous hold times (was on hold for 3+ hours before I gave up). You can see how it works in this video: https://youtu.be/_kiP6q8DX5c They got me connected to an actual IRS agent in about 15 minutes when I was trying to set up a payment plan for my unexpected tax bill last year. The agent walked me through several payment options I didn't know existed and helped me avoid some penalties by setting things up correctly. Given your tax amount, you might qualify for an installment agreement that makes this manageable without draining your savings all at once.

I need to eat my words from my earlier comment. After another failed 2-hour attempt to reach the IRS myself this morning, I reluctantly tried Claimyr. Within 17 minutes I was talking to an actual IRS representative about my payment options. The agent helped me set up an installment plan that works with my budget and explained how to avoid additional penalties. They also pointed out that I qualified for first-time penalty abatement which I had no idea about - that alone saved me over $700! Would have been impossible to know these options existed without actually speaking to someone. Still shocked at how quickly I got through compared to my previous attempts. For anyone facing a large tax bill, definitely worth talking to an actual IRS agent about your options.

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.

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.