A real simple way to help decide is to answer this question.
What two bands draw the biggest crowds at the squares?
Answer:
Rocky n the Rollers and
Uncle Bob's Rock Shop. The first band Rocky, performs 50's and 60's rock, which is the mainstay of the current developer owned station WVLG.
UBRS features music that is considered classic rock by most people. They can perform the Beatles and lead right into Jimi Hendrix to Led Zepplin to Pink Floyd followed by the Eagles.
Currenly I've only found one classic rock station WIND 95.5 out of Ocala/Gainesville. However, the station becomes weaker as you move south, and since I we often find ourselves headed toward Orlando, Clermont or Tampa I put XM/Sirius Radio in my car and really love it. I've got 18 present channels that I can go to at anytime. I would focus on the area between The Villages, Leesburg, Clermont and west Orlando for an area that classic rock could succeed.
I've been involved with music sales a good part of my life. I owned and operated a record store in Savannah, Georgia for almost ten years and operated a mail order CD/Record business for 20 years.