What other towns should I be thinking of moving to?

Probably not on your radar, but Spokane, Wa has a lot of the things on your list.

Tons of hiking opportunities here and close around Spokane and Coeur D'alene ID.

Lots and lots of water sports- fishing, paddle boarding, kayaking, jet skiing, boating at all the local lakes and rivers.

Several snow skiing mountains within an hour or so drive in the Mountains.

One of our top employers is health care.

International airport 20 mins from downtown.

4-6 hour drive to National parks (Glacier in MT, North Cascades National park WA, Olympic National Park WA etc...)
Summers are pretty mild with only a couple random days north of 90 degrees (unless you have a crazy pressure system that is affecting the whole west coast LOL) almost zero humidity.

Winters do have snow, but in the 19 years we've been here, only one winter was crazy where the city basically shut down due to the amount of snow received in 24 hours. It was the only year my kids missed school for a snow day. So it's definitely not normally brutal.

Lots of VBRO and airbnb opportunities.

As more and more people move here from California and the Washington Coast (due to housing costs still being lower than in those locations), the tide is turning on the political bent here. It's become much more liberal than it was when we first moved here and the people here are really nice. My dd lives in Ca with her dh as he is in the Military and one thing she always says when she visits is "gosh I miss nice people. No one where we live waves or says hi, everyone here does and I really miss it."

In 2018 we were in the 10 ten best places to retire list on Livability.com

Good luck finding your place to land! So many great places to consider!

My youngest ds is looking to buy his first house and just toured one in Greenbank! LOVE Western. When did you DH graduate? When were you there? We graduated in '87, education (me) and business admin (DH).

Eastern WA is very fire prone also.  I just got evacuation alerts for the Wenatchee area a couple of weeks ago.  So while Leavenworth, etc. are very pretty, be mindful of the fire risk.  If you lived in Everett, WA, we'd be neighbors!   If you were on Whidbey Island, I could wave every time I go to my favorite park! 

Friday Harbor, Washington. I could see it from my old bedroom. It’s beautiful and has a great PNW or Southwest Coast Climate. That’s how they do our weather. It’s cute, beautiful, climate is both summer and winter but neither are too severe and it’s amazing!

I love Park City, so beautiful, lots of shops and restaurants and wonderful views. That’s where I’d choose to live if I lived in Utah.

Park City is where I dream of moving someday. Great 4 season weather, easy access to a good airport (SLC), gorgeous scenery, historic town, skiing, hiking, access to so many national parks, good VRBO potential.

Another town that comes to mind for you is Saratoga Springs, NY. Four season weather, beautiful town, access to the Adirondacks for hiking, cultural opportunities (Saratoga Performing Arts Center), not far from NYC and other east coast cities. The Albany airport isn't great but it's fine.

The smoke from the fires can bet pretty terrible too even if the fires are miles and miles away.

I live on Vancouver Island and getting on and off the island can be a pain. We live with it but I had to wait 3 ferries aka 6 hours to get home and then it’s 90 min on the ferry and a 30 min car ride. That is my reality. I think having to park your car early to be sure to get off an island would be a deterrent. We walked over and parked our car in Sidney. I love Island living but you might not. 

From your list it sounds to me like Annapolis, MD where I've lived for the past 27 years marks all of your boxes except one. 

Scenic outdoors with hiking and access to water-here we live right beside the Chesapeake Bay-so that's a lot of water. Our town is known as "The Capital of Sailing" and sailing is everywhere from large sailboats to tiny ones like mine. There are all of the other water sports too. There is hiking also for those that prefer it, plus other outdoor recreation. We have a wonderful many acre park right in the city of Annapolis too for recreation called "Quiet Waters". 

Access to National Parks-There are 8 National Parks in Maryland including a National seashore on Assateague Island. 

A cute and interesting town-One of the many things I love about living here is the small city (more like a town) of Annapolis. The people are friendly and open minded. I would call most of us liberals. As far as the pandemic goes I have seen almost 100% mask compliance. We have many internationals living here too. On my mother's street she had folks from Holland and Germany living on the same small street at one time-for her this was heaven because she's from Germany. Also, Annapolis is one of the oldest towns in the entire country. There is a lot of history here and I find that very interesting-the architecture of the old town. 

No hot or humid summers-we do have hot and humid summers, but it's getting better. This year wasn't bad at all-much cooler than previous years. 

Cold winters but not brutal-check.

Largest healthcare employer in the area-we do have an excellent hospital right here in Annapolis, but also you've got access to John Hopkins in Baltimore (a 45 minute drive) and many more in Washington DC (a 45 minute drive in the other direction). University of MD. also has a trauma center. if that is what you need. 

Annapolis is a tourist destination so it'd be easy to use your property as a VRBO.

Airports-BWI International airport is about 35 minutes away and if you need it Dulles airport in Virginia is about an hour or more away. I use both. 

If you love water sports Annapolis would be perfect for you. If you are more into hiking (mountains) you might be better off out west or somewhere else. 

Whatever you choose I wish you well and happiness in your choice. 

Many places in Michigan: 
Grand Rapids (already mentioned)
Traverse City (or many other smaller towns along the coast - some would be conservative though)
Ann Arbor (expensive though)

Cannon Beach is beautiful but yes it’s cold and is also expensive. My cousins love it though, but one of them does drive far for a healthcare job. They usually take the train to the airport because it is far.
One of my friends just moved to Albany, Oregon and she likes it there. Her photos of hiking trails, make me want to go up there.
Another option is Washougal Washington. Nice small town feel and lots of trails to hike. Also far from the airport, and was a bit cold there. That was my major complaint.