5 Another thing to check - are you including your quarterly estimated tax payments correctly in your calculations? I found that was throwing off my estimates by a similar amount to what you're describing.

Another major issue I've noticed with online tax calculators is that they don't properly handle the nuances of business expense categories for self-employed individuals. As a freelancer myself, I discovered that many calculators either don't account for all the legitimate business deductions we can take, or they oversimplify how these deductions interact with self-employment tax calculations. For example, some expenses reduce both your income tax AND self-employment tax, while others only reduce income tax. Also, if you're claiming a home office deduction, that can significantly impact your tax liability in ways that basic calculators miss. The simplified method vs. actual expense method can result in hundreds of dollars difference, and most online calculators either don't offer both options or don't calculate them accurately. I'd recommend keeping detailed records of all your business expenses and maybe consulting with a tax professional who specializes in self-employment taxes, at least for the first year or two until you get a better handle on all the deductions available to you.

I ran into this exact problem with FreetaxUSA last month! The solution was actually in a totally unexpected place. Go to the "Federal" menu, then "Deductions and Credits," then "Adjustments." There should be a section called "IRA Contributions." In that section, there's a question about "you or your spouse being covered by a retirement plan" that affects both of your calculations. If that doesn't work, there's a workaround: enter a non-deductible IRA contribution instead. Since your wife's contributions were just for rollover purposes, they should be non-deductible anyway. You'll need to fill out Form 8606 for non-deductible contributions, but that might actually be the correct approach for your situation.

I had a very similar issue with FreetaxUSA last year! The problem is that the software sometimes doesn't properly link the retirement plan coverage between spouses when calculating IRA deductions. Here's what worked for me: Go to the "Personal Info" section first and make sure your filing status is correctly set to "Married Filing Jointly." Then, in the "Income" section, look for "Retirement Plans" and make sure you've indicated that YOU are covered by an employer plan. The key step I was missing was in the IRA contribution section itself - there should be a question that asks something like "Is your spouse covered by a retirement plan at work?" Even though you already indicated your own coverage, the software needs this information entered separately for the spouse's IRA calculations. If you still can't find it, try starting the IRA section completely over. Delete any IRA entries you've made, then re-enter them step by step. The software should ask about both your coverage AND your spouse's coverage during the interview process. Sometimes the questions get skipped if you jump around between sections too much.

Quick question - do you mail the 1040-X or can you e-file an amended federal return now? Last time I had to do this it was paper only and took forever.

From my experience as a tax preparer, whether you need to amend your federal return depends entirely on the nature of the error. If it was something like a state-specific deduction or credit that doesn't appear on your federal return, you're probably fine. But if it involved income, federal deductions, or anything that flows through to both returns, you'll definitely want to file that 1040-X. One thing I always tell my clients: when in doubt, amend. The IRS won't penalize you for correcting an error voluntarily, but they will charge interest and penalties if they catch it first. Since you already received your federal refund, if the amendment shows you owe additional tax, you'll need to pay that plus interest from the original due date. But if you act quickly, the interest should be pretty minimal. Also, keep good records of both your original and amended returns. The IRS sometimes sends notices years later asking about discrepancies, and having everything documented makes those situations much easier to resolve.

Has anyone used the IRS Sales Tax Calculator online? It estimates your deductible sales tax based on your income and location, then you can add large purchases like vehicles on top of that. Helped me figure out I wasn't anywhere close to itemizing being worth it.

Just to add another perspective - don't forget about other potential itemized deductions beyond just the car taxes! Things like charitable donations, unreimbursed employee expenses (if you're self-employed), tax preparation fees, and certain investment expenses can add up. I was in a similar boat last year after buying a car, and while the vehicle taxes alone weren't enough to justify itemizing, when I added up my charitable giving ($2,400), some medical expenses that exceeded 7.5% of my income, and a few other things, I ended up about $500 ahead by itemizing. The key is to do a quick calculation of ALL your potential deductions before deciding. Even if the car purchase alone doesn't push you over the standard deduction threshold, it might be the piece that tips the scale when combined with everything else you paid during the year.

Something no one mentioned yet - make sure you're using a qualified tax professional to help with your amendments during an audit! DIY tax software is fine for simple returns, but when you're dealing with audit+amendments, that's when expertise really matters.

One thing to keep in mind is timing - while you can file amendments for non-audited years, be strategic about when you submit them. I'd recommend waiting until you have a clearer picture of how your current audit is progressing before filing multiple amendments. If your 2022 audit goes smoothly and the auditor seems reasonable, that might be the perfect time to mention your intention to amend other years. On the other hand, if the audit becomes contentious or the auditor seems particularly aggressive, you might want to wait until after it's resolved to avoid any perception that you're trying to overwhelm them with paperwork. Also, make sure you have rock-solid documentation for all the amendments you're planning. The last thing you want is to file amended returns that themselves have errors or insufficient support. Take the time to organize everything properly - it's better to file one accurate amendment than to have to file corrected amendments later.