Do you write any additional info on the receipts? Sometimes I get receipts that aren't clear what they were for.

Great question! Yes, I absolutely write notes on any vague receipts right away while the purchase is still fresh in my mind. For business meals, I jot down who I met with and the business purpose. For supplies or other purchases, I note what project they were for. I also staple any relevant info together - like if I have an email approving a business expense, I'll print and staple it to the receipt. Makes it much easier to justify deductions if you're ever questioned about them.

I use QuickBooks for my small business and the receipt capture feature is decent. You take pics in the app and it attaches them to transactions. Not perfect but integrates well if you're already in that ecosystem.

Can you clarify how the tie-breaker rules work? I'm a Canadian citizen on TN status but have been in the US for 4 years. I was told I can't claim treaty benefits anymore because I'm clearly a US resident for tax purposes now.

Tie-breaker rules look at factors like where you have a permanent home, center of vital interests (closer personal/economic ties), habitual abode, and nationality. After 4 years in the US on a TN, it's difficult (but not impossible) to claim closer connection to Canada. You would need to demonstrate stronger ties to Canada than the US - permanent home there, family, bank accounts, voting, etc. The longer you stay in the US, the harder this becomes. Most tax professionals advise that after 3-4 years, you're likely a US tax resident unless you've deliberately maintained stronger Canadian connections. Filing Form 8833 to claim treaty benefits doesn't guarantee approval - it just asserts your position.

This is a really important point. My friend went down this road with a Cayman Islands setup for his trading business. Ended up with a full IRS audit, massive penalties, and had to pay all back taxes plus interest. The IRS agent specifically cited the lack of economic substance to the arrangement as the primary issue. Not worth the risk.

That's a really good point I hadn't considered. We calculated our support percentages based on total expenses for Mom, including housing, medical, food, utilities, etc. I'm pretty confident in our numbers (40% me, 35% brother, 25% her pension), but I'll double-check to make sure we didn't miss anything that might push either of us over 50%. Would this affect my ability to claim HOH?

As long as neither of you provides more than 50% of support, you're good for the Form 2120 multiple support agreement. Regarding your HOH status, that's separate from the support test. For HOH, you need to have paid more than half the cost of keeping up your home where your mother lived for more than half the year. This "keeping up a home" test is different from the support test. It only includes expenses for the home itself (rent/mortgage, utilities, repairs, property taxes, food eaten in the home, etc.). If you paid more than half of these specific home expenses, and your mother lived with you for 8 months, you should qualify for HOH even while your brother claims her as a dependent with Form 2120.

That sounds like a limitation of the software, not the tax code. TurboTax Premium handled this situation correctly for me last year. Some of the basic versions of tax software don't handle these more complicated scenarios well.

I haven't heard about this option. I'll definitely ask HR about it tomorrow. Do you know if there are specific requirements for a domestic partner to qualify under a Section 125 plan? Or does it vary by employer?

It does vary by employer, but generally they require proof of financial interdependence like joint bank accounts, shared lease/mortgage, or being named as beneficiaries on insurance policies. Some employers also require an affidavit that you've been in a committed relationship for a certain period (often 6-12 months). The key thing is that Section 125 plans allow employers more flexibility in defining eligible participants than standard health plans. Not all employers offer this option though, as it requires specific plan administration. Definitely worth asking about!

That's a pretty insensitive comment. There are many valid reasons people choose not to get married that have nothing to do with their commitment level. Financial considerations are just one factor in that decision.

That's really encouraging to hear! Did you have to do anything special on your tax return to make sure your parents could still claim you as a dependent? I'm worried about filling something out wrong and messing up my parents' taxes.

Nothing complicated at all! On your tax return (if you need to file one), there's just a checkbox that says "Someone can claim you as a dependent." You check that box, and that's it! You file your return, your parents file theirs claiming you as a dependent, and everything works out fine. The first year I filed, my dad helped me through it using TurboTax, and it was actually way easier than I expected. After that, I did it myself. When you're a dependent with a simple job, tax filing is usually very straightforward - just a few forms to fill out.

This isn't completely accurate. You're confusing household employee rules with self-employment. If someone is babysitting or doing lawn work as an independent contractor (which most teen jobs like this are), they need to file if self-employment income exceeds $400, even if they're a dependent.