If you’ve never taken 242 from McKenzie Bridge to Sisters, DOO EET. It winds through some seriously amazing huge lava flows from centuries ago and up top there’s a mountain observatory where you can see pretty much every mountain in WA and OR on a good clear day. And the section between the crest and McKenzie Bridge is super duper twisty and fun to drive in either direction.
Just chiming in because I stayed one night in Roseburg with my kids back in Sep during a road trip from Seattle to Sacramento. We stopped because:
- it was getting late
- Yelp had a Chinese restaurant review "I’m Chinese, and the food isn’t horrible and comes with really big proportions at affordable prices
Note: of the only value to the OP, this place delivers in case your folks need Chinese delivery.
- There was a bowling alley
- Holiday Inn Express
We stopped: the Chinese restaurant was as advertised (an old drive in burger place and did a huge take out business), we had fun bowling, and Holiday Inn was IIRC ~$89 with breakfast for 2 queen beds.
that sounds like it would be great fun - if someone else was driving and I could just relax and enjoy it.
it would have to be someone I trusted, of course. 
I have a very short list of people I’d sit passenger with on that road!
I truly appreciate all the responses.
watchwolf49, housing costs do seem to be a primary concern. I think they’re aiming to spend between $250,000 - $300,000.
Hunting and fishing are activities in the rear view mirror for my dad now. I think he would appreciate living in an area that reminded him of his halcyon days, but he won’t be doing any hunting. He might be coaxed to do some shore fishing from time to time, but that activity is good almost anywhere in Oregon.
SunnyDaze, I think they considered the Bend/Redmond area pretty seriously, but then decided that property values had put it out of reach. Personally, I’m lobbying hard for this side of the Cascades because what SmartAleq says is true: It’s tough to get over the mountains in winter. During a bad storm, I would be out of reach.
Agree with SmartAleq re driving over 242. It is stunning and everyone should do it. If you can catch the rhododendrons blooming along the McKenzie part of the drive, even better. Re the lava flow patch, it really makes you appreciate just how small we all are in geologic time. The lava flows where the observatory is built are between 2,600 - 2,900 years old, and they are obviously so young. Dee Wright Observatory
Highway 242 is closed from approximately November to July. You can get to Bend via the Highway 58 route mentioned, but those roads are also often closed down during storms.
China Guy, I appreciate your observations – glad to hear there is at least a passable Chinese joint in Roseburg! 
I don’t think my parents appreciate just how much access to good culture they enjoy living where they are now, and will miss it more than they realize when they leave. Even Eugene, despite a burgeoning food, wine and beer revolution, goes wanting in this department. (Much better now than when I moved here 14 years ago, but still. I defy anyone to find a decent Italian restaurant here.)
In all candor, I’m not sure my parents’ demands can be met. But here’s what I think they are, in order of importance:
Ready access (within 20 miles or so) to medical care
Housing costs between $250,000 - $300,000
Not too liberal
Access to cultural activities such as museums, good restaurants, theater, etc.
Less rain but not too much wind
Picturesque
LOL, I know… dream on!
Ashland fails the housing cost and liberalness factors; but they might get those in Medford and be close enough to appreciate Ashland’s cultural offerings. The Rogue valley is substantially less rainy, and quite picturesque.
I think you nailed it pretty well with Harrisburg–the only item you’re not going to get is the “less rain” part, but that’s a given so long as you’re on the wet side of the Cascades. It’s a fair sized town but outside of the liberal bastions of Eugene and Corvallis, yet close enough to enjoy the cultural advantages of college towns. It’s within striking distance of the coast, casinos (should that be a drawing point for them,) nature in its more benign forms and the very inviting wine areas to the north that are becoming genuinely picturesque. Giving a quick look at Zillow shows that with 300K as the top end there’s quite a decent range of good properties to be had–even more if you expand out to look in Junction City and Monroe.
Heck, for 350K there’s a duplex available so a potential for rental income if they’re so inclined or the second unit could be sold on its own. That’s a lot of house for not a ton of money. Fair number of foreclosures in the town too, if you’re patient and savvy you can get a lot for your dollar that way too.
I liked the Rogue Valley - it’s small enough you can live anywhere and easily drive to Ashland for all it offers. Jacksonville is charming.
1] Eugene is 75 miles away and she has a full service hospital … Portland has a big hospital … the rest of the state is only served by clinics and urgent care facilities … a fairly good chunk of Eastern Oregon has to go to Boise …
2] That much money will buy well about anywhere except the pricier neighbors in town …
3] The intense liberalism is found in Portland and Eugene and to a lessor degree in a few other towns … fair large swathes of rural Oregon run conservative …
4] I thought Eugene/Springfield area to be thin on cultural activities … Portland’s better … but for what you can find in Southern California, you’ll need to fly to Seattle or San Francisco … or Southern California …
5] Eastern Oregon for less rain, but the wind howls … the headlands on the coast take 100 mph gusts on occasion … the western interior valleys are mostly free on wind but it rains quite a bit …
6] Most picturesque north of the equator … we have everything in Oregon … desert, rain forest, tall mountains, volcanoes, ocean beaches, the second and third most spectacular canyons in the world, glaciers, hippies, we even have a decent airport in Portland …
Alas … we have earthquakes to make any Californian blush … 9.0M+ every 150 to 300 years … and it’s been 320 years since the last … so, any second now the entire state will turn to jello …
It’s an urban myth that Portland, Oregon is the only city with an active volcano within city limits … technically it’s a cinder cone and not expected to erupt anymore … good thing that … some other cinder cone, pretty much an any day type of thing …
The Big Feet only eat a handful of people every year …
“You know you’re in Oregon when more people own boats than air conditioners” = Jeff Foxworthy
I honestly wouldn’t recommend Medford to anybody. Miserably hot in summer, miserably cold in winter, and the place just looks ramshackle.
I found the winters very mild. I did think it was humid there, which the locals were surprised by, but I had been living in the western/dry part of Nebraska.
Medford gets a lot of grief but there is so much nice about it - I really don’t get the hate.
JackieLikesVariety, will you say more about what you like about Medford? I tend to agree with Chefguy, especially about the heat in summer, but like Roseburg, I don’t know much about the place except I try to avoid stopping at Harry and David’s. 
My parents had thought about it, but people kept referring to it as “Methford,” so they scuttled it from their list. I told them to do what I always do: Call the local Sheriff’s Department and ask them to give an overview of crime in the area they’re thinking of moving to. Criminal statistics are a matter of public record. Also worth keeping an eye on the local crime news in the local paper to get a better idea than just rumor.
Anyway, I’d love to hear what your experience of actually living there was, if you don’t mind sharing it.