Boy that's a tough one. There is so much beauty around both.
You mentioned Oldham County, now that area is spectacular with the best public school system in KY.
If you curious about the look of the area go to my pictures posted on
Welcome to Flickr - Photo Sharing (http://www.flickr.com - broken link) and just type in Oldham County, Kentucky, I am the "wandering photo nut", I have posted a whole set of KY pictures on there.
I have now been twice in the last 6 mths to KY to first time to investigate N.KY near Union & Florence, and also to see Lexington. The second time to re-investigate Lexington and then go up to the Louisville area to especially check out Oldham county. Can I say "Wow" one more time.
I could and did drive for hours on end just saying that. Now one person mentioned the size and traffic problems of Louisville, I actually found that to be the opposite. The highways compared to here in So Cal seem to flow decent even during high traffic times, but of course there are lots of beautiful scenic byways to take too if you want to mix it up. Twice I got stuck in "LA" like traffic in the Lexington area.
Once when everyone was going home and I was down by the Nicholasville area with a small one lane road that everyone attempts to use to get home [probably no choice in the matter], and the second time, in that Highway that circles the entire Lexington area "uggh", sat on that one for a extra hour to long, felt like I was back home here on the 405 freeway. No thanks.
We have found housing prices to actually be very similar between the two, depending on where you look of course. If you go to the outer nice suburbs they are always pricey, but of course the farther you go out, the lower the price. Don't think that Oldham County is "too far" from Louisville, once you go there like STX mentions, it literally would only take you probably 15 minutes from Crestwood or Prospect, and obviously if you go out as far as La Grange you are probably talking 25+ minutes. Still reasonable in my opinion to live in such a beautiful area yet still be close to the "big city".
I agree with you, Louisville would be my pick now after seeing both, but I still am very impressed with both. Lexington is just so clean!! Good luck on your choice. You will love it! I did.