According to the bugs list for Lucky 38 presidential suite on the FallOut Wikia this is apparently a known bug, unfortunately it seems the only suggested fix requires a certain level of progression in the story line:


  Sometimes, you can lose the option (or
  never be given the option at all) to
  tell your companions to wait at the
  Lucky 38 upon telling them to leave.
  It appears that if this bug presents
  itself, you will never be able to ask
  a companion to wait there for the rest
  of the game.(Verified, Oct. 31, 2010.)
  This can be fixed if you kill Mr.
  House and upload Yes Man into the
  system.


Why can't I send companions back to Lucky 38?
The rules of Pit are oddly contradictory. For n players choose n commonities, add in the Bull and Bear, shuffle and deal out the cards. The rules state that everyone gets 9 cards. Doh! With the Bull and the Bear added in that doesn't work.

The way we reconcile this is two people have 10 cards which gives them a significant advantage, e.g. they can simply hold a single card of a commodity to effectively eliminate whoever ends up going for that commodity.

Are there better solutions to this? 
