Wait, so even with the extension I still need to pay by April 15th? I thought the whole point was to give me more time since I don't have the exact numbers yet?

Yes, you still need to pay your estimated tax by the original deadline (usually April 15, though it varies some years). The extension only gives you more time to submit the actual return paperwork, not more time to pay what you owe. If you don't pay what you owe by the original deadline, you'll be charged interest on the unpaid amount from the original due date until you pay. It's not a huge penalty (currently around 7% annual rate), but it does add up. Make your best estimate and pay that amount when you file Form 4868. If you overpay, you'll get a refund when you file your complete return later.

This worked for me too! Called right when they opened and only waited 20 mins instead of the usual 2+ hours. The agent was able to see my W2 info in their system and gave me the numbers I needed for my extension form.

Does internet service count as a qualified expense? My son lives off campus and needs internet for his classes but I'm not sure if that's covered.

Internet service is a bit of a gray area. If your son lives off-campus, internet service would generally be considered a qualified expense ONLY if it's required for enrollment or courses at the educational institution. If the school requires students to have internet access to complete coursework or access required materials, then it would likely qualify. It's best to get documentation from the school stating this requirement if possible.

This is exactly right! I did the same thing with FreeTaxUSA and it worked perfectly. The software needs to see the qualified expenses first before processing the 529 distribution.

I appreciate the perspective, but I think there's a difference between choosing Starbucks for their coffee (personal preference) versus needing an alternative workspace because my home office becomes unusable during certain hours due to childcare issues. It's not preference - it's necessity for my business operations. From what others have shared and my research, it seems like the library miles might qualify under the "temporary work location" rule, especially since I don't go to the same library every time and the trips aren't daily. But I'll definitely make sure to document the business necessity carefully.

I see your point about necessity vs. preference, which is fair. The temporary work location rule might apply, but remember it's usually meant for places you don't visit regularly. If you're going to the same library multiple times a week, the IRS might view it as a regular workplace. My suggestion would be to document extensively why your home office was unusable on specific dates (maybe keep a log of when kids are home and why you needed to work elsewhere) and be prepared to demonstrate the business necessity. The conservative approach would be to not claim the library miles, but if you do, make sure your documentation is rock solid.

I track my business mileage with MileIQ and it shows you a map of your route. It might help prove you went straight from grandparents to library without personal stops. It's like $6/month but worth it for the peace of mind during tax time.

Does this HS code thing really matter that much? I've returned stuff before just marking "gift" on the customs form and never had issues. Seems like everyone's making this more complicated than it needs to be.

Yes, the correct HS code absolutely matters, especially for higher-value items. Marking returns as "gifts" is actually customs fraud and can get you in serious trouble. Gifts still have import duty thresholds in most countries, while properly documented returns using the correct HS code are exempt from duties and taxes. I learned this the hard way when I incorrectly labeled a return shipment and had it held at customs for three weeks. They eventually released it after I provided additional documentation, but the retailer almost denied my refund due to the delay. Using the proper codes and declarations from the start saves headaches and potential legal issues.

I've used DHL for returns from Thailand to the US multiple times. They're good but you still need to tell them specifically it's a return and provide all the documentation. Don't assume they'll automatically know how to code it properly! I always fill out my own customs declaration with "RETURNED GOODS" clearly marked and the proper HS code, then make sure the DHL agent understands what I'm sending.

For the delivery platforms, how do you handle this in bookkeeping? My accountant wants me to record the gross sales including their fees, but then that inflates my revenue numbers even though I never see that money.

For delivery platforms, you should record the gross sale amount as revenue, then record the platform's commission as an expense. This gives you accurate gross revenue reporting while still accounting for the fees. For example, if a customer orders $100 worth of food and the platform takes $30, you'd record $100 as revenue and $30 as a commission expense. Your net is still $70, but your books properly show the full transaction. This is important for accurate sales tax reporting as well as income tax purposes.

Good point about cross-state issues. I do deliveries in a tri-state area and ended up having to register for sales tax in all three states. What a nightmare! Each has different rates and filing schedules too.