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Maybe Athens, GA or Madison, WI. We weren't thrilled with Lexington, KY or Asheville. Ashville had a nice downtown, but it seemed sterile. Lexington didn't have a centralized downtown. It was more spread out. A few restaurants here, a few there.
Boise might be a city worth checking out becuase it fits all of the requirements you have listed. City population is near 220,000 and the metro population is near 660,000 with a lot of open space in and around the metro area.
I second Pittsburgh. It seems to fit almost all of your criteria, except for maybe extremity of seasons, which isn't really that bad. Winter can be harsh, but I've learned to like it, and I hated winter before moving here.
If you are squeamish about snow (which can be hit or miss in some winters), you are truly missing out on Upstate NY, which has everything you want. Try Ithaca, Rochester or Syracuse.
Any of the Front Range cities besides Denver fits your criteria. Fort Collins and Loveland have great medical centers and children's hospitals. Denver has probably the nation's best burn center hospital and people from around the country are flown there for treatment. As for hiking and stuff to do... it's The Rockies!
Little Rock might be a decent enough fit for you to look into. Actual city limit pop is 186k, metro area is about 600k. 4 distinct seasons but they can be pretty extreme, summers routinely in the upper 90's with several days over 100 and fairly high humidity. Winters with quite a few nights with nightly lows below 30. A good thing about our winters though is that we do get quite a few sunny days with temps in the upper 40's and 50's and the extra sunshine does wonders for the psyche vs. cloudier climes. Might be a bit extreme for you. Progressiveness...well it's not nearly as bad as some people might think but it's certainly not Portland! We do have top notch medical facilities here though with UAMS being the highlight: UAMS Medical Center - Arkansas Hospital - Little Rock Hospital - UAMS Health - University of Arkansas Medical Sciences
We have natural beauty in abundance. Sandwiched between two small "mountain" chains, the Ozarks and the Ouachitas, we have LOTS of rolling hills, forests, and natural streams giving you plenty of outdoor activities such as hiking, boating, fishing, plenty of golf, canoeing, kayaking, mountain biking...you name it. If this area can fulfill the entertainment needs of your particular younger person, well I think that would depend on what the younger person's interests are.
Now the kicker, you can easily get a new 4bdr 2.5 or 3 bath all brick home (use the 4th br as an office) and maybe even a "bonus room" for right around that $300k mark. Homes usually sell for around $90 - 110/sq ft range here depending on specific location, amenities, etc.
I second Little Rock. Don't let being in Arkansas scare you away. Crime is also very localized and not as sensationalized as protrayed in the 1994 documentary Bangin in Little Rock. Though its a conservative metro area, there are some progressive neighborhoods in the city proper that are very charming. One thing thats nice about Little Rock is how well the older neighborhoods of the city are integrated into their natural surroundings. Plenty of natural beauty and four distinct seasons. While many times in the winter we can see lows in the low teens and single digits, its not uncommon to have quite a few days with highs in the 60s even in January and Februrary. Winter usually starts to fade away around mid-March and the weather is beautiful April through early July. Biggest kicker about this area is its much more expensive to live in a decent area of Little Rock proper than it is to live out in the burbs, meaning you will have to make a decision between a bigger house in a very conservative cookie cutter suburb or a small more expensive house in a nicer, more charming and progressive neighborhood.
I might suggest Tulsa, Oklahoma but the population is higher than what you specified.
Lexington is one of the places I'd like to live. Beautiful scenery, and a large enough city to support many amenities.
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