Taxes are never fun.  In past years, especially since getting married, they’ve grown more and more complex.  The fact that both of us own businesses only complicate things further.  I use TurboTax to do our income taxes each year; it certainly makes the ordeal seem easier than what I remember of my father with papers sprawled across the dining room table.

After having our son in August, I was surprised to see a very small refund this year.  To be fair, every financial advisor in the world will tell you that the goal is to get as close to zero payment/refund as possible, but who doesn’t like to get money back, right?

Anyway, I was shocked that modeling different filing statuses wasn’t more intuitive in TurboTax, and changing filing statuses is impossible. You can run a what-if scenario to see how Married/Filing Separately compares with Married/Filing Jointly, but the model assumes your decision between taking the standard deduction or itemizing is the same that you chose in your current scenario.

In order to actually see both scenarios in the other filing status, you have to actually complete the returns again using the new filing status to see the results.  In our case, this meant investing another three hours of time.  Was it worth it?  In my case, I think so.

Update:  Ok, I realize this makes me a nerd, but a day or two after I posted this, I realized that I’d have to either recharacterize my Roth IRA contribution for 2014 or take a $330/year penalty since the income limit for Traditional or Roth IRA contributions is $10,000 when filing separately.  Yes, you read that correctly.  Eligibility phases out at only $10k.

Anyway, so after building a model that illustrated the taxes I would pay if I invested the $5500 in a brokerage account as opposed to a Roth, it was about $17,000 better to just file jointly.  I know, nerd.