Is a $100.00 fee for a job cancelled the day of the job appropriate
More than fair. I worked a deck job a few summers back and if it cancelled by noon of the same day ... there was NO $$$$$.
Do you prepare a contract? How do you handle repeat jobs?
With this new intense schedule, I suggest a simple contract. It's more of a reminder than a handcuff. A real pro will welcome a contract, and it can only help keep relations on a business level.
Are deposits required? What about open ended jobs with two weeks notice on either end?
No deposits are needed for repetitive work. Two weeks notice is more than fair for an ending. Some places don't give any notice, and that just stinks.
Booking agents... how do you work with them?
VERY carefully. They have a rep for taking advantage, so be careful. Make sure an agent cannot steal control of your room. They do it all the time. They promise tons of entertainers, and garuntees, so the house feels secure. All they see is the $$$$ though. Deal with care - make sure they KNOW that it is YOUR room to book.
For the most part - this will be an enjoyable adventure for you. You get the flexibility to set your own schedule, and fill in with subs when you need the time off. The times that you will hate it is when:
A) an act fails to show up ..... or
B) an act fails to entertain in the maner you are used to ...... or
C) an act decides to skate around YOU and go straight to the owners looking for more $$$ or control.
Be fair, but be careful. Good luck !