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 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.

Thanks for bringing that up. How exactly do you document 100% business usage? I literally only use this laptop for my business operations and have a separate personal tablet for everything else, but I'm not sure how I would prove that if asked.

The best way to document 100% business usage is to maintain a log showing regular business activities performed on the laptop. This doesn't need to be extremely detailed - just notes about what business tasks you use it for, which business software is installed, and perhaps noting that you have separate personal devices. It also helps to have the laptop purchased under your business name if possible and to keep it physically at your business location if you have one separate from home. If audited, the IRS is mainly looking for reasonable evidence that you're not claiming personal expenses as business, so even having clear separation of devices (business laptop vs. personal tablet as you mentioned) is good supporting evidence.

For partial business use like your 50/50 iPhone situation, you need to split everything proportionally. Since the phone is 50% business use, you'd depreciate 50% of the $1,100 cost (so $550) on your business taxes. For the trade-in, you'd calculate if there's any gain or loss on the business portion of your old phone (likely none if it's a typical depreciated phone).

Thanks for pointing this out! She already filed her return and I just texted her to check if she selected that option. I'm going to ask her to show me her return tonight so I can verify everything matches up with what I filed. Did you end up having to amend either return in your situation?

In our case, my son had to file an amended return to correct his mistake. He had checked "someone can claim me as a dependent" but also claimed his own personal exemption (this was before the tax law changes). It wasn't a huge deal to fix, but it did delay things. The most important thing is making sure all the facts are consistent across both returns. If she filed saying she can't be claimed as a dependent, but you claimed her, that's where the IRS gets confused and may flag both returns for review.

Do you need original documents or are copies/screenshots okay? I have similar issues with my nephew who lives with me but his mom claims him every year even though she barely sees him.

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.