Wouldn’t one of you clever yc types start up an online service to manage tax collections for small businesses? Since a lot of these folks are using third-party payment systems already, it seems like it would be a solvable problem.
Software solutions are not the answer here. Filing in 50 states, even if automated, exposes small businesses to time & money-consuming audits in 50 states. That is extremely undesirable but it will become a fact of life if this case goes the wrong way.