I'm at the point I'd like to throw my hat in the ring and see what happens. What is the most basic and affordable tournament I should be looking at that still counts for a rating? Would that be FIDE? USCF? Something else? Do I have to do one of those very expensive multiple day competitions or are there cheaper one day events that still come with official ratings?
A "real" rating is gained by joining the USCF and playing rated tournaments. You can get a rating from any USCF sanctioned tournament. They don't have to be all-weekend tournamants; I've played in several G30 tournaments that had 3 rounds in one evening. In addition, you and an opponent can play a rated match if a USCF tournament director approves it.
You can also get a (non-USCF) rating by playing on one of any number of internet sites.
EDIT - here are some clubs in Orlando. I recommend you join one and mingle. The first one here has USCF tournaments...
ORLANDO FL 32810 FL. CENTRAL FLORIDA CHESS CLUB (USCF ID A6007091). Affiliate Type: Club. Call for information. Call for information, ORLANDO FL 32810. Contact: HARVEY LERMAN. Contact Phone: 407-644-3542. Club Phone: 407-629-6946. Address: C/O HARVEY LERMAN, 921 N THISTLE LANE, MAITLAND, FL, 32751-3736. email: email@example.com. Web Site: www.centralflchess.org, Club Membership Not Required, Casual Play, USCF Rated Events, Blitz Events, Club Championships, Private Lessons Offered, Under Age 18 Welcome, Prison chess support. (Crosstables from past rated tourneys for this affiliate)
ORLANDO FL. ORLANDO CHESS & GAMES CENTER (USCF ID A6018039). Affiliate Type: Club. 10AM-10PM MON-SUN. 8853 COMMIDITY CIRCLE, ORLANDO FL 32819, ORLANDO. Contact: ALEX ZELNER. Contact Phone: 407-248-0818. email: firstname.lastname@example.org. (Crosstables from past rated tourneys for this affiliate)
1) any tournament sanctioned by the uscf is rated. For the first 23 (IIRC) games your rating will be provisional, meaning it's calculated using a different formula than normally. After that point the rating will be calculated as usual.
2) uscf sanctioned tournaments can run for a week or more, or they can be over in a matter of hours. The most prevalent format seems to be 5games in a weekend, but I used to run a one-day seven-round event (and was asked once to make it 10 rounds in a day).
3) aside from the separate events, most clubs run tournaments that have anywhere from 1-4 games in an evening, and continue weekly for several weeks.
I guess the short answer to your question is "it depends."