It's illegal because of the DMCA. It's not legal to sell tools that bypass copy protection.
You wouldn't need to send your phone or anything, you can do fully remote jailbreak from a web browser with the right exploits.
You'd be surprised how popular pay-to-jailbreak shops are/were in places where this isn't enforced. You go there and the guy jailbreak your phone in front of you then hands it back to you. There's absolutely a market