Bo, this isn't aimed at you, just getting my thoughts down overall...
For me, it's NOT the software part. That's two technical problems -- collecting it and remitting it. 9000 different tax zones based on geocodes x 5000 different products which may or may NOT need sales tax collected each depending on 46 different state tax codes which change often.
After collecting it, I'm sure these "authorized service providers" will take some XML file and then e-file 46 different state sales tax returns each month for some "reasonable" fee. Compliance issues will follow which means we get audited by folks where we have no representation. That's plain wrong.
It's also not fair. If it's so easy, and NOT a burden, why can't EVERYONE do it? Why exempt anyone? Every IN-STATE brick and mortar retailer has to collect it, regardless of size. Why should a $999K a year retailer NOT have to collect sales taxes?
The DOT COM BIG BOYS see it this as a cash cow. THey want it because they want to offer software solutions to collect and remit the tax. Also, they're having to collect it anyway, so they also don't want smaller to medium sized guys to have the competitive advantage of NOT having to collect it.
I thought the SUPREMES settled this decades ago with mail order businesses not having to collect taxes from states in which they don't have a business nexus.
I've ALSO heard that this is a back door to tax EVERY SINGLE FINANCIAL TRANSACTION which should be freaking some folks out.