I have no clue how Billy handles money but he has won far more than this in action matches already. He had possibly the best stakehorse in the country for two years with the green light to play about any match he wanted.
The bar definitely is. There is now a full bar with seating about 3 feet from the escalators. I dislike the smoking, but it was a great place to hang out and socialize.
Dry land. It literally starts outside the tournament room. If you exit the main room and head towards the elevator, a 10 foot detour will place you in the chair of a slot machine.