Filing taxes with all these accounts....

[MoonLiteNite]

So i am about 30. I have always done my own taxes with turbo tax every year since i was 18.
Normally it takes like 15 full mins to do. Tack on an extra 5mins when i bought my house, and another 5mins when i was getting a deduction for solar panels.

But last year i did some day trading, and oh boy was that some serious typing. The etrade document wouldn't import properly so i had like 10 pages to copy and past over...

And now this year.... I have LC, LC w/ IRA, vanguard IRA, tax retirement account, day trade account, sold over 25k worth of ESPP, and looking into the "Saver's credit" and i had some income with youtube/twitch.tv AND drove for uber.
I call myself a smart person, great with computers. But will taxes be a pain to actually do? Or is it just a bit more typing than normal? What if i forget to append something onto turbo tax?

[mskyle]

I don't think it's *difficult* work, just irritating and fiddly and boring. My most difficult tax year to date I had three jobs, game-show winnings (which meant I had to fill out two state tax returns), reimbursed moving expenses and a handful of investment transactions. It sucked, and I did the state returns in the wrong order and ended up having to overpay and get refunded, but it wasn't the end of the world.

[Spork]

Every time you add something new, it will be a pain.  That's just taxes.  And if you have to hand type your trading account again... it will be a pain.

But, it will also be a pain to pay an accountant to do that typing for you.

Forgetting something on a return is also not the end of the world.  Amending a return (especially with Turbotax or similar software) isn't a big deal.  I've had to amend things occasionally in years passed due to getting required forms extremely late or getting amended forms from banks/etc. 

[MoonLiteNite]

So i guess simple, just time consuming....
I really was thinking of paying someone to do it this maybe. Maybe they can get me discounts or rebates that i do not know about.

If i do file alone, i will be using the paid for version of turbo tax this year.

[jwright]

You can attach the list of all of your trades to your efiling documents and then you don't have to itemize every single one. 

I don't use turbo tax, but every software I have used has had this option.   You mail in the Form 8453 with copies of the detail attached. 

[MoonLiteNite]

You can attach the list of all of your trades to your efiling documents and then you don't have to itemize every single one. 

I don't use turbo tax, but every software I have used has had this option.   You mail in the Form 8453 with copies of the detail attached. 

Yeah, etrade has the export option, and turbotax (paid version) had an import option for etrade, but it was only reading the first page of data. I did have the option of actually mailing the paper document in, but a family member has worked part time for IRS, her job was to be a monkey and type in data from those sheets into the computer. She said 80% of the clowns there had sucky slow typing, and lots of type0s. So i

So do not trust that...