You can usually get flight following in North/Central Florida. Depending on your route you may get handed JAX-DAB-ORL App, or Daytona may be skipped.
I'd say the odds of being refused entry to Orlando Bravo are very low. However--especially coming from the north--the frequencies can be jammed something terrible; you may have to steer clear until you can integrate yourself into the chatter.
For the record, you don't have to enter Orlando B to get to Leesburg from Craig. JAX Center or Orlando Approach may, in fact, vector you to stay clear of the Bravo, or may give you a lower altitude to stay under it. Even if they do clear you, expect to be vectored around.
Two final things: when you're on with JAX, ask them if R-2910 is active. If it isn't, staying clear of Orlando Bravo en route to KLEE is much easier. Second, as rick mentioned, there's a lot of training activity around Sanford and Leesburg. If you have an extra radio or aren't using flight following, it may behoove you to monitor 123.50.