@dlowan,
If you really like someone and have a good time with them, what's a little high maintenance, as long as you can control the amount of exposure you get to it?
The bit I'd find irksome is the high-handedness with people who can't answer back.....when I was waitering I don't think I'd have been able to resist a very smart arse response to having someone dictating the number of ice cubes....but c'mon, these folk can be wonderful friends.
On ya for being strong with the hotel, JC.
Hope you all have a great time. And Mm.....no killing the visiting friend, ok?