That's really good to know! Do you have any recommendations for keeping track of all these potential deductions throughout the year? I feel like I might be missing stuff.

I just use a simple spreadsheet with categories for each potential deduction - mortgage interest, property tax, charitable donations, medical expenses, etc. I update it monthly so I don't forget anything. Some tax software also has year-round tracking features or apps. The key is being consistent about saving receipts and documentation. I take photos of donation receipts immediately and save them to a specific folder. For medical expenses, I request year-end summaries from all my providers. It's also smart to check your itemized deductions against the standard deduction amount mid-year to see if you're on track to benefit from itemizing.

Not all points are deductible though. I learned this the hard way. Points for lowering your interest rate are deductible, but points that are really just fees disguised as points aren't. Check IRS Publication 936 for the full details.

Didn't they actually try to make a "postcard-sized" tax form a few years back? Whatever happened to that? Seems like my tax return gets thicker every year.

They did try to make that simplified postcard form around 2018 as part of the tax law changes. It was basically a marketing gimmick - they just moved all the calculations to separate worksheets and schedules that you still had to fill out. The whole thing was abandoned pretty quickly because it actually made filing more complicated, not less. Now tax returns are definitely getting thicker every year with more worksheets and schedules than ever. The 2023 tax year is no exception with all the special credits and deductions they keep adding without simplifying the old ones.

Try using tax software. It walks you through all that stuff step by step. TurboTax, H&R Block, or even the free options like FreeTaxUSA handle all those worksheets and calculations behind the scenes.

That's incredibly frustrating to learn! I had no idea there was actually a proposed system that got killed by industry lobbying. I just looked up that ProPublica article and wow... the fact that other countries have been doing this for decades while we're stuck manually entering numbers that the government already has is ridiculous. Do you know if there's any movement to revive this idea? Seems like the kind of common sense thing that both political parties could potentially get behind.

There have been several attempts over the years, most recently the Tax Filing Simplification Act that's been introduced a few times but hasn't passed. The current administration has made some promises about simplifying the tax filing process, but meaningful change faces the same powerful lobbying obstacles. The Free File agreement was actually modified in 2019 after the ProPublica reporting, removing the provision that explicitly prevented the IRS from creating its own system. That's a start, but there's still strong resistance. The best hope is continued public pressure and awareness - the more people understand that better options exist and are being deliberately blocked, the more momentum builds for change.

This makes me want to move to Australia just for the tax system lol. Do they at least buy you dinner before they take your money? The US system is just insult to injury - "figure out how much you owe us or go to jail, but also we won't make it easy, and ps we already know the answer.

Thanks for this advice. My income has actually decreased quite a bit since 2022 (lost my higher paying job). Would that potentially help me qualify for an Offer in Compromise? And is that something I can apply for myself or do I need a professional?

Yes, a significant decrease in income could definitely help qualify you for an Offer in Compromise. The IRS looks at your current income, expenses, asset equity, and future earning potential to determine if you can reasonably pay the full amount owed. You can absolutely apply yourself using Form 656, though it's a complex process requiring detailed financial documentation. There's a $205 application fee, but it's waived if you meet low-income certification guidelines. If you decide to go this route, be extremely thorough with your financial information. The IRS rejects most offers that are incomplete or don't accurately reflect your ability to pay. There are good resources on the IRS website to help you through the process if you want to try it yourself.

Did they charge you a lot in penalties? I'm in a similar situation and worried about how much extra I'll end up owing beyond the original taxes.

Thanks for the advice! Just to clarify - are there income limits for Roth 401k contributions? I thought those were just for Roth IRAs.

You're absolutely right, and I should have been clearer. There are no income limits for Roth 401k contributions - those limits only apply to Roth IRAs. With your combined income, you would likely be in the phase-out range for direct Roth IRA contributions, but your Roth 401k contributions are completely fine regardless of income level. That's one advantage of the 401k version.

I wouldn't delay a major life decision like buying a house just for tax reasons. The benefits of homeownership typically outweigh any short-term tax optimization.

Good point. I guess I was just thinking about our experience where the timing of our home purchase affected which year we could first claim certain deductions. But you're right - probably not worth delaying such a major life decision.