Players that are active should use the fort barracks instead of the hotel.
The barracks level 1 provides the same benefits as a hotel level 5; the difference is that in the barracks you sleep for 6 hours instead of 8.
Each additional level adds a 6.67% increase in benefits (energy and health) over the hotel.
Move to the fort, work the jobs around it; when you have enough money saved up, go back to town and deposit it into your bank account. You'll benefit by having a quarter horse, but probably you have that already. "Enough cash" is different from player to player, and is the maximum amount you're comfortable carrying around and risking to lose. For me is about $500.