More-or-less lifelong Roseburg resident here. There’s at least one other regular Doper that lives here as well and judging from SmartAleq’s post there may be more than just us two. 
I’m having a very hard time judging the “drier climate” comments made above. We get lots of rain here—lots and lots of rain. This winter has been particularly dry, but this is far outside the norm. Last time I looked we average about 30 inches of precip per year, almost all of that rain between November and June. Snow is quite rare. I’ve never felt the summers to be humid, but maybe I’m just used to it.
Roseburg is more than “semi-Trumpian.” It is a very conservative place—after the 2015 school shooting Obama came to visit the survivors. There was a rather large street protest when he arrived, with people waving confederate flags and big signs suggesting he move back to Kenya. At least one of the county commissioners openly and publicly supported these people.
The economy is depressed and while it’s a lot better than it was a few years ago jobs are still less than plentiful. The economy hasn’t been timber-based in many years. I work at the local community college helping adults with job-search skills, and right now the biggest employer is the VA. A good chunk of the population works in healthcare or customer service. Douglas County is quickly running out of money and the county commissioners have publicly stated that soon the only thing they’ll be able to keep running is the courts and the sheriff department. The entire county library system shut down last year after residents chose not to pass a bond that would help keep them open, which has already had a noticeable effect on the community.
A lot of younger people have trouble finding work, although drug use that legalization of marijuana has a lot to do with that as well.
Trying to think about this from the perspective of a retiree, I’d say there are some significant negatives, the two principal one being a) essentially no public transit (and especially for things like wheelchair pick-ups for dr. appointments) and more significantly b), there’s only one hospital and it has a quite deserved reputation for being rather shitty. While there are a few medical specialists a lot of patients have to travel to Eugene or Medford for specialized medical care. There’s a VA hospital here but it also sucks—a scandal of theirs regarding failure to treat patients recently made the New York Times. The few retirement homes / nursing homes are also of quite poor quality (and please believe me when I tell you the healthcare services here truly do suck as I speak from experience). The upside is it’s probably easier to live here on a fixed income, especially if one has secure housing.
There is a positive to living here, namely the outdoor recreation opportunities. One is never more than hour and half away from… well, pretty much anything you’d want to do. The Pacific Ocean is an hour to the west, the North Umpqua provides fishing and hiking and whitewater rafting, and pretty much everyone hunts. There’s mountain climbing in the cascades and even some spelunking opportunities town near Tule Lake.
Personally I’d rather retire in the heart of a big city and not a jerkwater town where it rains 8 months out of the year, there’s no real theater, the most diverse grocery store is Safeway, Red Robin is considered haute cuisine, and the only hospital within 75 miles sucks. But that’s just me.
It’s a tiny little farming town that frankly doesn’t have much to recommend it on its own beyond comparatively inexpensive real estate adjacent to the Willamette River. There is a decent diner and an unexpectedly good Thai restaurant. And a superb butcher. It’s also somewhat more moderate politically.