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I can entirely understand why Stripe doesn't deal with taxes. They're insane. I was involved in implementing a site that sold off-site discount parking reservations near airports and dealing with taxes was certainly no fun. And this was restricted just to the US. There is a national consortium of states that makes getting state sales tax slightly easy.... but all the services that offer the ability to look up tax rates didn't cover the service we were offering, parking reservation. So we had to investigate the rates ourselves... and it's a good thing we did. Some counties or municipalities have created special taxes to apply specifically to this kind of service in order to make things more expensive so that parking at the airport isn't such a terrible deal.... oh and those laws don't stay static, of course. You have to keep on top of them, and modify your code/data/whatever when new laws take effect or old laws are repealed.

The most fun was when an area in Texas passed one of these laws taxing parking near airports (even if that parking is offered by a hotel or some other established business... if it has shuttle service to the airport, it must be taxed) but all the various people offering parking through our site didn't want to comply with the law, so they wanted us to not charge the tax to customers! Worse, the business types wanted to actually cater to these scofflaws. I refused to implement it though, because that's just stupid. We'll collect the tax, if the clients don't want to actually pay the municipality, that's their business... but we do have to keep track of who charges it, how much, when those rates change, etc... it's a a bit of a pain, and even the services dedicated to tracking this kind of stuff are not comprehensive.

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