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.