Taxachusetts.

It’s tax time again, and I’m doing my annual patriotic duty. Having sold a lot of stocks and bought a condo in 2005, last year was the first time my taxes were ever even moderately complicated, so I tried out Turbo Tax. I was pleasantly surprised at how easy they made the whole process, and thought it was well worth the twenty bucks. Granted, I still did the state taxes by hand, but with the federal forms done it was pretty straightforward.

So, this year the big complication was that I got married, and my wife moved from Rhode Island to Massachusetts while only earning income in Rhode Island. To complicate things further, she had some extra income from some free-lancing she did on top of her regular job, which had to be treated as a personal business. I figured the state taxes would be kind of a mess because she had to file in both states, so I went ahead and bought Turbo Tax ($20) with the two state downloads ($30 each).

What a waste of money.

The fundamental complication is that we’re filing jointly for the federal form but have to file separately for the state forms, since we lived in Massachusetts for different fractions of the year. This completely confused Turbo Tax, which imports the information from your Federal forms to do your state forms. So, I got clever; as a work-around, I redid my wife’s federal form from scratch as if we were filing separately so that TurboTax would import her information properly into the state forms. Well, I don’t have any idea what we did wrong, but Turbo Tax completely screwed up her Massachusetts form…in the end it tried to tell us she didn’t owe anything to Massachusetts, but even a cursory review of the Massachusetts instructions made it obvious that this was just plain wrong. In the end, we ended up doing both of our Massachusetts forms by hand, and working through both the Federal and Rhode Island forms that Turbo Tax spit out as well to convince ourselves that they weren’t screwed up too. There’s no question that Turbo Tax made it worse, not better.

So, if you’re going to bellyache that you have an unfair tax burden, I’ll tell you to go cry me a river. But if you want to complain that taxes are just too damn complicated, I’ll listen. I don’t have a problem with writing a check; I do have a problem with wasting four Sundays figuring out the exact amount the check should be for. Can’t we just say I owe the state, say, a fifth of what I owe the feds and just be done with it?