Your con sense post was really good (and man, as someone who used to do housekeeping, THANK you for the hotel staff is not your mom), but one thing I would be a little concerned about is your rooming with multiple people not registered with the hotel thing. It's a good idea to have a backup plan (read: cash) if you intend to sneak people into a room, cuz depending on the place it's real easy to get screwed over by a particularly vigilant desk clerk. Had it happen in NYC and that shit *sucks*.
That’s a really good point! It’s good to A) be careful about it and B) be able to afford the actual cost, even if you don’t want to or plan on paying it. It hasn’t been a problem for me ever but it’s always good to be aware that shit can go sour.