Good question. Some of this depends on who owns, or rents, the airplane.

Overnight stops incidental to instruction are allowed, as long as legit instruction is occurring.


Two issues with your proposal...

- If you do not stay with the student on the overnight, then it would start to look more like flying for hire and less like flight instruction.

- You repositioning the airplane is flying for hire. Only exception would be if YOU owned or rented the airplane, in which case you would have to be concerned with commercial maintenance requirements for the airplane. It is actually legal for you to get paid to repo someone else's plane.

This one might actually be a grey area, I think it could go either way. I suspect it would come down to the legitimacy of the flight instruction...if there was a real need for it that the FAA would buy off on, you would probably be OK. But if it was one of those "wink, wink" kind of deals it could bite you in the rear.