they give you, I'll do it for cheaper!
Ha but in honestly, I'd ask about their
-familiarity with the route
-familiarity with the vessel or similar vessels
-at least 2 or 3 recent references from folks who they've sailed with
-how they're going to choose a crew and if the crew will be paid
-and sometimes I like to ask people about the most significant challenge they've overcome while sailing offshore
too, just to see what they say.
Often with routing, crew number, expected travel time/cost and such, I'll have a plan already formulated then ask the skipper or crew for their own opinion.....see if it matches up with yours! If they give you a proposed route that fights the Gulf Stream
the whole way, maybe they don't know what they're doing. Or if they, for example, say that Chesapeake to BVIs is a 20 day trip....and they need to be paid by the day....maybe they're not the right person either.
All in all, it's all about trust. Get to know the person before committing to anything because like you said, they are having the pleasure of bringing your boat
to you, and that boat is your life! If I can go have a beer
with a guy before committing to a job, that's the most tried and tested way of deciding who I want to sail with.
Hope everything goes well for you! And remember, I'll do it for cheaper!