One thing nobody has mentioned is that contribution limits for HSAs in 2025 are going up to $4,150 for individual coverage and $8,300 for family coverage. If you're under 55, that is. There's an extra $1,000 catch-up contribution allowed if you're 55+. Make sure you don't go over these limits or you'll have to deal with excess contribution penalties (6% tax on the excess amount). Your employer contributions COUNT toward these limits too! That tripped me up my first year.

I think people are overcomplicating this. I use FreeTaxUSA for my taxes and it asks simple questions about my HSA that make it super easy. No need to manually fill out Form 8889 or anything like that. The software does it automatically based on your W-2 info and any additional contributions you made outside your payroll.

Wait, so all moving expenses aren't deductible now? I moved last year for a new job that was 300+ miles away. My tax guy said I could deduct it?? Now I'm worried I'm gonna get audited.

Has your friend considered taking the Section 195 startup cost deduction? The IRS allows you to deduct up to $5,000 of business startup costs in the first year (subject to limitations if total startup costs exceed $50,000), with the remainder amortized over 15 years. Some of his expenses might qualify if they're directly related to investigating or setting up the business.

One thing that nobody mentioned yet - check your final pay stubs from both jobs! They won't replace your W-2s, but they can help you verify that the information on your W-2s is correct, or give you estimates if you're missing a form. Your last pay stub of the year often has year-to-date totals for: - Total wages earned - Federal tax withheld - State tax withheld - Social Security and Medicare taxes I've caught mistakes on W-2s before by comparing to my pay stubs. It happens more often than you'd think, especially with smaller employers!

I made a huge mistake my first time filing with multiple W-2s. I only reported one of them thinking I could just do the other one later or something? Anyway, I got a scary letter from the IRS months later saying I underreported my income and owed more taxes plus interest. Don't be like me!! Make absolutely certain you include BOTH W-2s when you file. The IRS already knows about all your jobs because your employers report that info directly to them. If what you report doesn't match what they already know, it triggers automatic flags in their system.

Has anyone considered getting a part-time W2 job to offset some of the SE tax burden? I'm currently doing this - 20 hrs at a coffee shop plus my freelance work - and it helps because I'm not paying SE tax on that portion of my income.

If you're in a common law marriage in Texas, DEFINITELY file jointly! This was a huge help for me and my partner. My self-employment income combined with her W-2 income put us in a better overall tax situation, plus her withholding throughout the year covered a lot of what we owed. Don't hesitate on this one.

Former H&R Block employee here. Just wanted to add that there's a middle ground between the "do it all in front of you" approach and the "take everything and come back later" approach. Many independent tax pros (including some CPAs) will do an initial meeting to collect docs, then work on it, then schedule a review meeting where they walk you through everything they did and answer questions before filing. That way you get the benefit of their focused attention when preparing it AND you still get to see and understand what they did before it gets submitted. Just ask about their process when you're interviewing potential CPAs!

One thing nobody mentioned - CPAs tend to be way more expensive than H&R Block. I switched last year and paid almost triple what I used to pay. For me it was worth it because the CPA found deductions I never knew about that more than covered the difference, but just be prepared for sticker shock!