I don't like the so-called "sharing economy" because they're intentionally skirting the rules and saying that they don't apply because 1) we use an app; 2) we use the internet; 3) we're different; or 4) just, well, BECAUSE. Sorry, but...
If you're paid to repeatedly drive strangers someplace in your car, then you're a taxi or limousine operator and should be properly regulated, licensed and insured.
If you're paid to repeatedly house strangers in your home, then you're an innkeeper and should pay applicable hotel/motel taxes.
If you're paid to repeatedly fly strangers where they want to go in a plane, then you should have a commercial certificate, acquire appropriate insurance and operate under Part 135. This is a far cry from finding a couple of guys to split the gas to OSH.
Dancing around the rules doesn't make you look smart - it makes you look like a smart ass.
If you're paid to repeatedly drive strangers someplace in your car, then you're a taxi or limousine operator and should be properly regulated, licensed and insured.
If you're paid to repeatedly house strangers in your home, then you're an innkeeper and should pay applicable hotel/motel taxes.
If you're paid to repeatedly fly strangers where they want to go in a plane, then you should have a commercial certificate, acquire appropriate insurance and operate under Part 135. This is a far cry from finding a couple of guys to split the gas to OSH.
Dancing around the rules doesn't make you look smart - it makes you look like a smart ass.