Piggybacking on that, I stumbled on a UA marketing bit for what they call "Signature Service", which I gather is a fee-based personal concierge type of offering, which may be useful for this type of scenario as well, if you're worried about navigating an unfamiliar airport and ensuring all of the above proper transfer of bags and all that. No idea of pricing--surely it is a king's ransom!--but as above, YMMV.