3 Is there a specific format the IRS requires for this gambling log? Can I just create a spreadsheet or do they want something more formal? Seems like a lot of work to track every single bet.

19 There's no official IRS form for the gambling log, so a spreadsheet works perfectly fine. The key is consistency and detail. For occasional gamblers, it's not too burdensome, but I understand it can be a lot if you gamble frequently. For high-volume bettors like sports gamblers, most online platforms allow you to download your complete betting history, which the IRS will generally accept if it contains the necessary details. The personal log becomes more important for cash games and situations where electronic records aren't automatically generated. The IRS mainly wants to see that you're tracking your activity in a systematic way.

25 Wait, so you're saying even if I deduct $15k in losses against my $82k win, my AGI still goes up by the full $82k? That seems really unfair!

What about if one spouse is self-employed with a Schedule C business and the other is W-2? Does that change the calculation at all?

In a self-employed and W-2 earner situation, filing jointly is usually still more advantageous. The self-employed spouse can still take all their business deductions on Schedule C regardless of filing status. When filing jointly, you might actually benefit more from certain deductions like the Qualified Business Income deduction, which can be affected by your combined household income. One scenario where separate filing might help is if the self-employed spouse has potential audit concerns or inconsistent income reporting that could create tax issues. In that case, the W-2 earner might want to file separately to avoid joint liability. But strictly from a tax savings perspective, joint filing typically results in a lower total tax bill even with a Schedule C business involved.

I've used it and it works pretty well. Just make sure you have your most recent paystubs and last year's tax return handy when you use it. The calculator will tell you exactly what to put on your W-4s. My husband and I both earn around $65k and we had to add about $80 additional withholding per paycheck each to break even.

Could you explain how to actually calculate this with an example? I'm trying to do this math myself but getting confused about where the bracket cutoffs are and how to determine the additional amount needed.

Sure! Let's use 2024 tax brackets for a single filer as an example. The 22% bracket goes from $44,726 to $95,375, and the 24% bracket is $95,376 to $182,100. If your first job pays $85,000, you're already in the 22% bracket. When you add $55,000 from the second job, your total is $140,000. So $95,375 - $85,000 = $10,375 of your second job income is still in the 22% bracket, and the remaining $44,625 is in the 24% bracket. The additional tax you'd owe is: $10,375 × 22% = $2,282.50, plus $44,625 × 24% = $10,710. Total extra tax of $12,992.50. If you're paid biweekly (26 paychecks), you'd need about $500 extra withheld per paycheck to cover this. You could either check the multiple jobs box on one W-4 or add an additional amount to Step 4(c).

I use it regularly and find it pretty accurate, but you definitely need your paystubs and last year's tax return handy. The key is entering the information exactly as requested. For the second job, you can enter the expected annual salary and $0 for withholding so far if you haven't started yet. The estimator will then tell you exactly what to put on each W-4. I've found it gets me within $100 of my actual tax bill every year.

This is such good advice! I learned this the hard way too. I keep a spreadsheet now tracking all expenses for my dad who lives with me. I also have him pay his portion of expenses from his account directly to mine with notes like "Dad's share of utilities" so there's a paper trail.

This happened to my grandma too! She had like $20 in dividend income from some ancient account she forgot about and it caused such a headache with the IRS. They're really strict about everything being reported properly.

I've heard of those but never tried them. Are they user-friendly at all? I'm definitely not a tax expert but I can follow instructions. Do they do the math calculations for you or do you have to do everything manually?

They're somewhat user-friendly - definitely better than paper forms, but not as guided as commercial software. They do handle the math calculations for you, which is a huge help. They also perform basic error checks before you submit. The main challenge is knowing which forms you need. For your situation, you'd need Form 1040, Schedule 1 (for the HSA contribution deduction line), and Form 8889 for HSA details. The system doesn't tell you which forms you need - you have to determine that yourself. But if you're just dealing with W-2 income and an HSA, it's manageable.

H&R Block moved HSAs to their "Deluxe" tier last year. I tried them and got the same upsell treatment as TurboTax. They start you on the free version then halfway through hit you with "upgrade to continue" when you enter HSA info. They're all playing the same game unfortunately.