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I lived in Ashland many years, first town I lived in ORegon. Beautiful scenery in those Siskiyous. IMO, Medford, is a great place not to live, unless you enjoy being in a place overrun by meth labs, increasing property and gang crime and in general, ugly and with no personality. If you don't mind a liberal, pagan, yuppie , weirdo atmosphere, Ashland is for you. Ashland and Medford for me are two opposite extremes.
I found Grants Pass to be a real beautiful area and not so whacky as Ashland. You can find some more real, less superficial people in towns like that and not sacrifice beautiful scenery.
I, myself am just growing tired of most small towns in Oregon though. If you want some diversity and not to just be in a liberal hippy/yuppie mecca, perhaps you can consider Salem, Corvallis or Portland. I just moved to Bend and the scenery is unbeatable and not as dreary weather as Ashland. Plenty of free range. Although, there seems to be a yuppie elitist circle in this town, like Ashland. I am going to explore the surrounding towns like Redmond, Prineville for perhaps a more down home , small town indigenous Oregon feel.
If you want to buy a house, houses crashed in Ashland and this may be a good time. $1,000,000 house 8 years ago is now like $700,000. Although, who can trust buying any real estate with the economy?
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