Hiring a retrieve crew - thoughts? US

I'm pondering the notion of hiring someone to be a dedicated retrieve
crew for days when I'm planning on going XC. I was thinking maybe a HS
senior or perhaps college student.

Hourly rate would be paid and any expenses covered related to the task.
If I'm not headed too far out, they could hang at the gliderport, do
homework, whatever unless I landed out. If so, they'd use my vehicle to
come get me.

If I decided on a straight out flight, then they'd head out with the
trailer as soon as I left the local area on task.

The upside for them is that on a good day it's easy money with no real
work involved. On a long day it might be a late night getting home and
no guarantee on making the party that night.

I'm betting some on this group might also come up with some risks that I
haven't thought about in this situation. Some obvious things include
finding someone dependable and able to safely drive w/ the trailer.
There may be issues with car insurance that I'm not thinking about.
Maybe some additional issues with liability present too.

Let's not waste time discussing why I would prefer not to just depend on
other glider pilots at the club, but I'd really like thoughts on this
basic concept, particularly if you've got some legal basis or real world
experience that you can draw upon.

Thanks in advance,

Gary