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I'm originally from Ashland area, which is a drier climate but lived in Eugene for a couple of years, so I am used to rainy weather. I'm not too concerned about the weather there. My partner is interested in being able to commute via motorcycle most of the year. Of course, there are rainy days here too, but then we also have 2-3 solid months of too cold/snowy weather during which he can't ride.
I'm also interested in learning more about the surrounding small towns/communities around Bellingham. We're definitely interested in purchasing property with a good amount of acreage (5+ acres) and I'm not sure we would find that in Bellingham..
If you're okay with the weather in Eugene, you're likely okay with Bellingham, with a couple twists- it doesn't get nearly as hot in Bham in the summer as the proximity to the ocean (or at least, Puget Sound/Salish Sea) moderates things a bit more, and we're occasionally subject to Canadian cold fronts moving down the Fraser Valley in the winter. But overall, it sounds like you'd be fine, and your partner would still be able to ride much of the time.
Regarding real estate, most of our past searches have been for places in town, but we've looked quite a bit in the surroundings, as well. It gets rural quickly out of town, so it's all about your threshold for distance from town/amenities and what you're comfortable with. Within a short distance you can find things that feel like they're a million miles away. I'd look in Whatcom County (near Ferndale, Deming) AND I'd also consider Skagit County. The Mount Vernon/Burlington area is close to Bellingham, centrally located to the islands, and access to the North Cascades. And again, the options vary from coastal wetlands to farmland to island, mountain or lakeside, so I'd definitely recommend a trip to explore.
I lived in a town of 35,000 and many or most of the longtime residents were related. Some were actually close cousins and you would never know it. If you get crosswise with one you might start to have issues with another and not know why. There were a lot of transplants but many only stayed a few years. Most of the young people left town when they could. Some came back to raise their kids there. I lived there 35 years and was only being accepted toward my last few years (first name basis with bankers, pharmacist, librarians, etc.). It is hard to fit in if that is what you want.
There were some pretty big families which adds to the family connections. I had a friend who moved to a neighboring smaller town and went to the PTA meeting and complained about the poor turnout. People looked around and counted 22 noses and said "this is it, everybody is here". She had two kids and everyone else had six or seven all in school.
Manitou might work. "Small town" if you stick to it and don't constantly slide into CS (metro of 700k). But you can do that if you want. Or possibly look further out at Woodland Park.
"small town/small-town feel". Most feel it (good & bad) in towns of 2-10k population. Some might feel it in a town / area of 50k (kind of a stretch). Some could think they have it in a metro of 500k compared to what they are leaving. This is possibly your biggest choice. What city amenities do you actually use / care about (besides an airport)?
You might consider Prineville, Madras and La Pine OR if you really want small town/small-town feel in central OR. Though you might think the first two look too dry. Sisters, Oakridge if you'd go even smaller.
Tahoe country is a big area with many style niches.
You probably won't consider it, but Spearfish SD is another option.
Lots of folks put a high priority on easy access to a major airport. Maybe it makes sense for them (depending on how much they fly and how much hassle they can take in stride), maybe there is too much emphasis on it. Can limit choices quite a bit.
Work and housing situations vary quite a bit among your study locations.
-close to an airport; its about 30 minutes to COS airport, just under 2 hrs to DIA
-Mountainous area; the town proper it sits in a valley of the foothills. It does have outlying developments actually up in the mountains such as Cedar Heights or Crystal Park. Manitou has steep, narrow roads that can be a challenge in the winter. As is parking. If you have multiple cars, trucks, trailers, Manitou will be a challenge.
-small town feel; sure. It also is fairly overrun with tourists in the summer and many places close over winter. It also is not physically separate from Colo Spgs. They run together and you will be going into west Colo Spgs for most/all shopping. West side of Colo Spgs is not as kitchsy as Manitou but is quite a bit different than the rest of the city.
-dog friendly; pretty much. There are a few places, as a local, you can probably bring your dog into, but its not like a ski town dog culture. There are dog friendly restaurants in Colo Spgs.
-four season; yes, sometimes all in one day. weather here is highly variable. It can snow in October and May, but can be shorts and flip-flop temps in December and February. Because Manitou is in the bottom of several valleys, it can be prone to flash floods, although they have made some big improvements to mitigating these risks.
-lakes/ponds for skating; not in town. Green Mtn Falls 20 minutes up Ute Pass from Manitou does have this. If you live in Crystal Park (gated, restricted community), they also have this. Otherwise, its indoor rinks in Colo Spgs.
-near tracks for motorcycle track days; dirt or asphalt? dirt track is on the far east side of Colo Spgs, about 40 minutes away. National Forest for cruising is within 10 minutes. Asphalt requires you travel to Fountain CO, Pueblo, CO, Denver CO, or Strausburg CO.
Also near here to the west of Manitou; Green Mtn Falls, Chipita Park, Woodland Park. Up I-25 from Colo Spgs; Monument, Palmer Lake, Woodmoor.
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