Tax Returns: Sort of like Craps!

So for the first time in eight years, I decided to do my own taxes.

Last year, I watched the guy at H&R Block fumble around the keyboard for three hours. I could see his mind working:

Hmmm...  Message box says, "Enter email address".  Ok.  

D...  E... V... I... N...

Where is the "at" sign?  Oh, there it is, above the "2".

I kept asking him what I would consider to be pretty routine tax questions, and he kept having to go ask somebody else. At one point the other person came over, at which point I realized the blind was being lead by the blind.

"Do I have to enter *every* one of these stock sales?"

"Oh, you don't have to do that. The IRS doesn't care. Just put the totals, and enter 'see attached', and include the report from the broker. I never do that for any of my clients, and I'm pretty sure none of them ever get audited. That will save you a whole bunch of time."

Shortcuts. I'm sure the IRS loves those.

Anyway, this year I downloaded TurboTax. Having not used tax preparation software since the 1990's, it was an interesting experience.

There's this box that's always on the screen that says "Your Refund" with the amount you're getting back in big green letters (or red if it's how much you owe). And the number changes as you're entering information. It's kind of nice in that you get an idea as to how different deductions affect the outcome.

But it's kind of feels like being in Atlantic City.

1. You enter your W-2 data, and you get this *huge* green number. Wohoo, it's like you hit the Jackpot!
   
2. Next you enter your dividends, and the number goes down a little. Ok, no big deal.
   
3. Then you start entering your stock transactions, and you spend the next two hours watching the number trickle down to zero, and then it turns red and starts increasing again. Watching the red number get bigger and bigger is definitely not as fun as watching the number get bigger when it's green...
   
4. You enter the mortgage interest and other deductions and the number starts to come back up towards zero. You're now at the point where you'll just be happy to break even.
   
5. The night is over. You didn't lose as much as you thought you would. Now you can hit the free buffet (or in my case, eat a peanut butter and jelly sandwich).
   

Anyway. It's done. I just have to review the final documents, and compare them against last year to see if I have to file an amended return to unfuck what the guy from H&R block did. You know, little things, like how he didn't bother to ask if I had an IRA...