1. K-1s. If someone had said to me when I was contemplating an investment in a partnership requiring K-1 reporting: "Nords, come with me to watch us do our taxes!" I would probably have not invested. I have four of five K-1s. I'll probably see #5 in July.
2. 1099-Qs and 1098-Ts for college expenses.
3. Redeeming I/EE bonds tax-free for educational purposes by having to launder them through a 529. It turns out that "educational purposes" for I/EE bonds is either tuition or a 529. "Room & board" can only be paid from a 529.
4. Qualified Higher Educational Expenses (QHEE) can only go as high as the college's on-campus room & board fees, even if your student is living off campus. If your student goes to summer school then you have to get the special summer-school QHEE rates for your documentation.
5. Points paid to refinance a 30-year mortgage must be deducted over the life of the loan. Unless you refinance, but of course you probably paid points for the new mortgage too.
6. BofA will tell you on your 1098 all about how much your mortgage paid in principal & interest, but not how much they paid for your insurance & property taxes out of your escrow account. This makes it tough to fill out Schedule E for your rental property. Luckily I happened to save their four-page two-point-font escrow analysis statement. Unluckily I happened to use the "projected" numbers instead of the "actual" numbers, but I eventually caught my mistake.
7. Mileage tracking of vehicles used for (a) a Schedule SE business, (b) a rental property, and (c) volunteer work.
8. Having to document home energy improvements all the way back to 2006 to make sure that you don't exceed the cap on some improvements (like energy-efficient windows & doors).
9. For our familyroom renovation, the contractor ordered an eight-foot lanai door along with 10 windows. It's all on one invoice and it's not broken down by individual items. The tax code gives separate tax credits for "energy-efficient doors" and "energy-efficient windows". Luckily Home Depot had prices on their website.
10. This seems like a good place to end the list, so I've saved the "best" for last: TreasuryDirect lets you convert paper savings bonds to electronic bonds by mailing them in. However they give you a separate "conversion account" that's linked to your regular account. At tax time, you have to find the two separate website pages containing one 1099 from your regular electronic bond account and a second 1099 from your conversion electronic bond account. You happen to get two e-mails about the 1099s, but they're darn near identical and you just have to be smart enough to go looking for the conversion account 1099.
When I'm feeling demoralized about all of this, I say to myself "It could be worse: you could still be doing the taxes for that non-profit, and sending out their 1099s!"
Originally Posted by TromboneAl
Anyone notice the unconventional rounding? $3.50 is rounded to $3 instead of $4, $3.51 is rounded to $4.
Sounds like a convention to me...
Originally Posted by pb4uski
My gripe is after paying for TurboTax also having to pay an additional $20 to have my state returns e-filed.
When I was w*rking I typically had to file in 3-5 states depending on where I worked that year and would get back $10-30 from each state. It seemed to me to make little sense to pay $20 to e-file to get back $10-30, so I print out and mail each state other than my resident state.
Now that said, my only tax preparation costs are TurboTax, e-filing fees and my time so I guess that I don't have a lot to gripe abut in the whole scheme of things.
Imagine how much worse it'd be if you had to pay an accountant for that tax prep...