Well... Richmond is more progressive like Lexington.. about a 25 minute drive and has about 30,000 people. Less expensive to live than Lexington, but has most of the amenities you'd probably want.
Paris is a really small town, but about 20 minutes to Lexington. Don't know a lot about Paris, but the road for a commute to Lex, has been improved and widened in the last 5 years and is beautiful. Just really peaceful there.
Mt. Sterling. about 30 minutes from Lexington on I-64 commute. Smaller town, but more factory type layout of the town. This is the first "flat" town after driving East towards Lexington, past Morehead (which is in the foothill mountains). Have not been there, but have heard many good things about this town. Might be worth a look-see anyway.
Winchester.. within 20 minute commute. Nice smaller town, with some amenities as well. Looks very pretty in the housing sections of town. Heard there is a major drug problem there, but I really can't that Winchester would be any worse for that type of crime than any of the towns that were mentioned. If it's something you're into... that's what you'll get. If you don't have much to do with drugs or druggie types, I don't really see it as being a huge problem for most people. Petty crime and property crime seems to be the biggest noticeable factor related to a lot of drug dealing in these areas. *shrug*
I think in comparison Kentucky has it's faults as all states do, but my opinion is.... it has WAY more advantages to living here, than most other states, so good luck, and I truly think you will find you DO want to live here, in spite of it's scars!