Lexington, from what I've experienced there, isn't horribly homophobic, but it's like pretty much any place I've been in America (22/50 states). There are some pretty sweet music venues that I've been to in Lexington - Cosmic Charlie's is definitely worth a visit, I'd say. Bar + Music, and it's for ages 21 and over, so you don't have to deal with as much of the University crowd as a lot of other places in the city.
And from what I remember, cab fare is pretty decent there. There are always good things available in hotels which give you the names and numbers for takeout, cabs, and local attractions. They're pretty accessible.
I'm about an hour and a half or two hours from Lexington myself, but I spend a lot of time in Richmond or Berea, with trips to Lexington for concerts and to visit friends who go the University of Kentucky.
It's a pretty nice place. Have fun!
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