Hmmmmmmm...
Schools: Pikeville Independent, Raceland-Worthington (near
Ashland) are decent. Russell Independent (also near
Ashland) is pretty good. Out of more than 60 school systems east of I-75, these are the only three even worth mentioning!
Shopping: Well, if shopping entails Macy's, Target, Dillard's, and other "non- Wal-Mart" establishments, then...
- Mt. Sterling, Owingsville, Stanton, Clay City, Mt. Vernon, and Irvine are all within 45 minutes of Lexington.
- Raceland, Greenup, Ashland, Louisa, Olive Hill, and Grayson are all within 45 minutes of Huntington, and 1 hr. 15 min. of Charleston.
If shopping means Von Maur, that will require a trip to Louisville. Neiman Marcus or Saks, go to Cincinnati.
Affluence: Pikeville and Greenup County (home of Raceland, Greenup, and it's near
Ashland) are the only fairly affluent places east of I-75. Mind you, "affluent" is not the same here, nor is it really as extravagant, common, or even nouveau, as it is in places like the suburbs of Boston, DC, or Dallas. "Affluent" means some leftover old money from a few established local businesses, as well as Ashland Oil's engineers, former execs and supervisors, etc. Not that I care, really, but that's just what I've observed.
The only truly affluent areas of the state are found in pockets in and around Louisville, Lexington, Frankfort, and northern Kentucky.
Golf courses: What town doesn't have one?
By the italics you can tell where I'm going, right? Recommend the Ashland area.