Cost: Aiken (B-), Ocala (C-)
In my experience, Aiken is between half and one-third less expensive than Ocala. A solid dry stall that costs $400 in Aiken costs $700 in Ocala. Gas, groceries, hay, shavings, and living quarters are all cheaper in Aiken. The only things that I think are equivalently expensive are top coaching and vet care. Both locations are more expensive than most other places.
Weather: Ocala (A), Aiken (B)
Ocala is 20 degrees warmer than Aiken and you never (hopefully) have to worry about snow in Florida. Both have good enough weather to ride outside every day.
Coaching Quality: Aiken (A), Ocala (A)
The reason that Aiken and Ocala are the two top US winter training location is because they have the top selection of coaches. David in Ocala and Phillip in Aiken draw the top riders, who are themselves good coaches, and a trickle-down effect takes over.
Nightlife: Ocala (B), Aiken (C+)
The Horse and Hound wins it for Ocala. Even though the H&H is overpriced, overcrowded, and slow, you can always have a good time visiting with friends because absolutely everyone goes there. Your other options are a cowboy night club and hip-hop bar combo, and Tony's Sushi (which is really tasty). Aiken has karaoke night?
Footing: Aiken (B+), Ocala (B)
Both Aiken and Ocala are sandy, so they handle the rain very well and never get rock hard. When most other places are muddy or covered in snow, sand looks good. Aiken has better hills for conditioning, while Ocala is almost completely flat.
Aiken folks will tell you Ocala stinks, and vice versa, so lets put it up to a vote:
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