If I had the funds I'd love to do this. I'd only do it with a regular though. And it would be at least an overnight. I'd make sure she had some "down time" (eg, let her alone for an hour to do whatever) and had her own private space (eg, if hotel adjoining rooms w her own bathroom, or a second bathroom if my home). Also likely have some non-sex event scheduled (movie, sightseeing, etc).
The hazards include revealing true identity, as one cannot book an airplane ticket with a working name. Likewise, the client might have to reveal his name too (airline personnel may say it, if in ones home there may be things w real name on it).