I know it seems silly to worry about 99 cents, but I just want to make sure I'm doing everything right. Better safe than sorry when it comes to taxes! Thanks for the straightforward advice though.

Trust me, I get it. I used to work myself up over tiny details on my taxes too. My accountant friend always says "report everything accurately but don't lose sleep over pennies." The IRS is looking for major discrepancies, not whether you properly categorized less than a dollar. Cash basis is right anyway for most regular people.

It's because different types of income have to be reported on specific forms. The 1099-B is specifically for proceeds from broker transactions (buying/selling investments). The 1099-MISC Line 3 "Other Income" is for things that don't fit elsewhere - like referral bonuses, interest on uninvested cash, or promotional rewards. The IRS requires brokers to categorize each type of payment correctly. It is confusing though - I agree the system could be streamlined!

Oh wow, that's really good to know! I hadn't thought about that. I have a Chase Sapphire card - do you know if they treat tax payments as regular purchases? And is there any way to confirm this before I make the payment?

Chase Sapphire definitely treats tax payments as regular purchases! I've used my Chase cards for this exact purpose multiple times and always earned the points with no issues. You can confirm by either calling the number on the back of your card and asking directly, or check their terms and conditions. Most major card issuers also have this info in their FAQ sections online. Just search for "tax payments" or "government payments" in their help section.

Are you 100% sure about this? I thought I read somewhere that credit card convenience fees could be deducted as a miscellaneous expense?

This is a great point that I hadn't considered. We've been together for over 10 years and have the kids together, but you're right that it's always smart to think about all scenarios. Do you know if such an agreement would have any impact on how the IRS views the gift? I want to make sure anything we do on the relationship side doesn't create tax complications.

An agreement about what happens to the gift in different scenarios shouldn't change how the IRS views the gift, as long as the gift is complete and no strings are attached at the time it's made. The key from a tax perspective is that you're not expecting anything in return. However, if the agreement makes the transfer look more like a loan or conditional payment rather than a gift, that could potentially create issues. Make sure any agreement you create clearly states that the transfer is a completed gift for tax purposes, and any terms about future scenarios don't make it conditional in a way that would undermine the gift status.

Recipients generally don't report gifts as income or file any special forms. It's only the giver who has to file Form 709 if the gift exceeds the annual exclusion amount (currently $17,000 per person). The girlfriend would just receive the money tax-free. This is one of the nice things about gifts - the recipient has no tax consequences or reporting requirements.

I hadn't thought about the state education department! That's an excellent suggestion. Did you have to request the letter specifically or did they have some kind of standard form they provided?

I had to make a specific request for the enrollment and tuition verification letter. Most state education departments have procedures in place for closed institutions, but you need to ask for exactly what you need. When you contact them, be sure to request both enrollment verification (with specific dates) and an itemized statement of all tuition and qualified expenses paid during the tax year. Be prepared to provide proof of your son's identity and your right to access his records, like a birth certificate or his signed authorization if he's over 18.

This! 100% this! Same thing happened with my brother's trade school. The main website was gone but the separate student portal system (run by a third-party) stayed up for document access. Worth checking if they used common systems like Blackboard, Canvas, or dedicated student financial portals.

Do you know if either version handles gifted stocks properly? I received some shares from my grandpa this year and I have no idea what the original purchase price was. Will Deluxe help me figure this out or do I need Premier?

Gifted stocks is exactly the kind of scenario where Premier provides more detailed guidance. Deluxe will allow you to enter the information, but Premier walks you through determining the proper basis for gifted stocks with specific questions and explanations. If you don't know the original purchase price, you'll need to either get that information from your grandfather or his broker, or determine the fair market value on the date of the gift. Premier has specific screens to help with this situation, while with Deluxe you might need to research the rules yourself. This is definitely a case where the extra $20 would be worthwhile.

FreeTaxUSA is great but I found their interface for entering lots of stock transactions to be really tedious compared to TurboTax. If you only have a few trades it's fine, but I had like 50+ transactions and almost lost my mind entering them manually.