Medford has grown quite a bit since I last lived there. I did go to college in Ashland and would visit the mall (they would have a VW show inside) and parts of Medford.
You'll be in the Rogue Valley. Lightening storms, colorful sunsets, hot summers (peaked at 105ยบ a few times when I was there) and cold winters (snow/ice). A good variety of seasons...much better than Portland! Lots of deciduous trees like oaks so the fall season is colorful. The area tends to be a little on the red-neck side for me. Ashland is a nice, small tourist town along with the college. Klamath Falls is serious indian and red-neck territory. The area has plenty of country roads that would be just a blast in a topless teener and plenty of days for it to boot. If you love the great outdoors, including camping/hunting/fishing then you'll love it there! Lots of that stuff to go around and then some! Unfortunately, the ocean is about 2-3 hours away which is pretty far for me but much closer than where you currently are

Skiing at Mt. Ashland is okay. Tends to be icy. Oh, the Medford airport is an "international" one but it's $$$ to fly from it compared to real international airports like Portland and Seattle. There's a Coors distributor there as well so you can get cheap beer -- remember, I was a college student down there
Personally, I like it down there far more than here in Portland. But the job market is better for me here and all my car buddies are here as well. There is a VW club down there as well:
http://www.sovw.com/ I have seen the occasional 914 for sale in that area but none ever driven. I would recommend it.