Filing Sales Taxes Online

Just finished up preparing our sales tax returns for October.  We file in 9 states (Oregon does not have a sales tax) and about 5 municipalities or counties.  Being located outside of cities cuts down on the number of separate returns we have to file, but being in the lodging business adds returns (there are a lot of local lodging taxes out there).  NONE of these taxes work the same, and every return is unique.

I am working on a longer post with some observations about sales taxes, the states that have it right and the states that are over-complicated messes.  However, in the mean time, one observation.  Most states offer an online filing option.  If every state had a nice online tool, or better yet, a tool I could upload data to right out of Excel, I would love it.  This is a true win-win, with the business owner saving time and the state saving LOTS of time by not having to re-key handwritten returns.

However, several states currently have awful, totally non-intuitive online filing systems, or systems that are down all the time, or systems that make correcting errors a real pain in the butt, or all three.  The problem is, in most states, there is no way to try before you switch.  Many states play a kind of brinkmanship, requiring that if you file even once online, you can never go back to paper.  I did this with one state and the online tool really sucked, and now I am stuck  using it, despite the fact that their paper return is easier to use.

So, as a result of this nutty requirement, despite being totally committed to doing things online, I sit here filing paper returns, too risk-adverse to play Russian Roulette with various states' online filing systems.

  • Max Lybbert

    Out of curiosity, could somebody start a small sole-proprietership selling, say, chocolate bars, and then file the online sales tax as a trial to see if filing your entire operation's sales tax online is worth it? Sole-proprieters selling chocolate bars do go out of business all the time. ...