1) Yes free room and board, along with a stipend (I believe monthly). In addition, you can work as an OA up to 10 hours per week to make additional money (~$7.50 per hour, depending on min. wage)
2) January, on quarters, May change this year (source =
Resident Advisors (RAs) : University Residences and Dining Services)
3) It's fairly competitive, but I know of quite a few people that became RAs. Just depends on how outgoing / fun / experienced you are.
4) I'm not 100% sure, but maybe 20-30 hours?
5) Definitely become an office assistant (OA). It's a pretty good stepping stone to becoming an RA. Also get involved within a residence hall--each one has their own council. These are great ways to become friendly with a Resident Manager (RM) or Hall Director (HD) that can make it much easier to get hired.
Links:
6) Yes
7) If you cannot file your taxes by April 15th, be sure to file for an extension.
Cheers!
(Note: I was an OA for 3 years, but never applied to be an RA)