Have you considered a yurt? I stayed in one for several days in the winter in the mountains of Colorado and it was quite comfortable. I have some neighbors who are using one while they build a cabin.
If it is all about paddling venues, relatively lower cost, and relative proximity to a variety of ocean venues and urban amenities (health care, cultural resources, etc), I would look at the west side of Rhode Island, near the Connecticutt border.
I wanted to relocate to RI in my retirement for the plethora of (rough water) ocean venues. But wife’s preference and maintaining geographic closeness to our families kept us in Boston. (I think the paddling is great here too, but the cost of living is NOT inexpensive.)
-sing
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Look around the northern and eastern edges just outside the mountains. Lake effect snow predominantly falls to the east of Lake Ontario. Syracuse and Watertown average around 120 inches of snowfall per year. The tug hill plateau area gets the worst of it, that’s the upland area between the eastern shore of the lake and the western edge of the Adirondacks, where the average annual snowfall exceeds 200 inches. Lake Placid gets about 100. But the towns along Rt 11 that I mentioned in an earlier post only get around 70 inches, and Plattsburgh averages 75.
Property within the Adirondack Park is expensive. But home prices are very reasonable just outside of the mountains. The west edge is very snowy. I don’t really know the Mohawk river towns on the south edge of the Adirondacks other than what I can see from I-90. That area has been economically depressed for decades. On the eastern side, from Albany up through Lake George housing will be expensive and you can expect a lot of people and traffic. North of that, it gets better.
One place I would look is around Potsdam, Canton, and Colton. That gives you access into the park from the northeast on Rt 56. There’s also the Grass and Raquette rivers to paddle there. Canton and Potsdam are college towns, which I kinda like.
A second place to look is around Malone, which is on Rt 30, a major road that takes you straight to some of the best paddling in the Adirondacks. You can get from Malone to Paul Smith’s and the St. Regis Canoe area in just over 30 minutes. Malone’s not the most happening place though, the local economy is correctional facilities and farms.
The third place I would check out is along the western side of Lake Champlain. It may be a little further drive into the park, but you have more options. Plattsburgh is a bigger town with more places to eat and shop. You can take the ferry from there to Burlington. Also, I-87 runs through there and takes to you up to Montreal in about an hour (plus border time) or down to I-90 in roughly 2 hours.
Lake Champlain is nice too. We go camping in the area most years and have been casually looking at a second home on the Vermont side of Lake Champlain with the thought of retiring there.
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Lakes, not ocean. Rhode Island has only 5 lakes over 100 acres.
I grew up in the shadow of Tug Hill, very familiar with those massive snow storms.
Don’t forget to factor property taxes, and energy and other expenses. I have a house in a Maine coastal community, but I’m not waterfront. A quarter mile from salt water and about a mile from open ocean. And my property taxes are quite low. I expect it’s because there are so many high-value waterfront properties, and they essentially subsidize the taxes for lower valued houses like mine.
I lived in Saranac Lake from about '05 to '15. It’s where I got (a little bit) serious about paddling. Almost endless choices, and almost all are limited to non-motorized watercraft. But, the paddling season is short, and it can get wicked cold (-30 F) in my yard more than a few times. Ave about 110" snow per year (remember, the winter Olympics were held just down the road in Lake Placid (1932 and 1980). I enjoy winter sports too, so that doesn’t bother me. On the other hand, prices are lower (but still high by upper midwest standards) and climate a milder in the St. Lawrence Valley (north of the Adks). Lots of great paddling, especially around where the St. Lawrence River flows from Lake Ontario (Thousand Islands region).
I recommend you vacation several times in any prospective place at various times a year to see for yourself if you like it.
I recommend you consider distance from family and friends. Don’t know your age or time in life. But experience tells me that if you’re close to parents, children or grandkids emotionally distance makes that decision difficult. Many times I’ve seen retired grandparents move back up north from Florida to be near grand kids…in January.
Raisins kayaks at night to avoid Florida summer heat. But his record for consecutive kayak days is in the high 400s. Can’t do that in Minnesota.
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I have spent 2 weeks in the Adirondacks for 25 years, usually the end of August and beginning of September. It’s incredibly beautiful then with endless paddling opportunities and usually good weather. A friend that lives up the described the year as follows.
In October things begin to freeze up followed by ice and then heavy snow and frigid temperatures. In late April things begin to thaw ushering in mud season. May through June is black fly season with mosquito season through July and most of August. Then the second half of August and the first half of September is usually beautiful.
Areas with beautiful paddling tend to be very hot in Summer with plagues of biting insects or have year round cold water like the PNW or Maine. Many have a short paddling season without cold water gear or it being too hot and humid in summer. Some coastal areas are very windy.
Most areas have great paddling some of the time, but not year round. The length of the warm water paddling season can vary greatly.
I’m not very familiar with inland lakes.
On the West Coast you can paddle all year.
Same for the Southeast.
I paddle/play all year… on/in salt water. It’s been well over a decade since the last time Boston Harbor frozed. But, inland waters are obviously different. My western ME camp is near huge lakes, small ponds and white water rivers (I mostly indulge do more white water than flat water when I am there). Some of the observations noted about seasonal limitations about NE inland waters and land based challenges are spot on.
-sing
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I would say they are a little bit exaggerated. October is usually a great month for paddling.
Mosquitos are anyplace you want to paddle on flat water. They are easy enough to manage and haven’t been an obstacle to my family enjoying paddling and camping over the week of July 4 every year.
But the black flies and no-see-ums can be bad enough in the late spring and early summer that they might keep you inside for a month of nice weather.
I personally agree that October (or anytime water is NOT frozen) is a “great” time to paddle. But, it’s subjective and dependent on a person’s relationship with chillier/colder air and water temps, and how well they are prepared and dressed for these. Generally, in the 30 plus years of having my camp in the Western Maine Mountains – 20 minutes from Lake Umbagog and 15 minutes from the South Arm of Mooselookmeguntic Lake – I can say that the area generally experiences the first snow fall and frigid overnight temps by mid October. Granted that these may be slowly moderating with climate change. Reflecting the change, this year’s Umbagog ice out was the earliest ever on March 27.
Since having closer access to the ocean is not an issue, there are some decently priced (again, relative judgement) houses can be found around the many little towns and smaller city (Lewiston/Auburn) in the Western ME area. Decent hospital care would have to be found in Portland, ME., which is around 1.5 hours by car from ME/NH boundary in Oxford County. The fact is that younger folks are leaving these areas because of the lack of good paying jobs.
-sing
There are a lot of places where you can paddle all year as long as the water remains liquid, but I prefer to paddle without needing cold water gear. However, I will wear a drysuit if needed. Just getting lazy in my old age I suppose.
Consider a move to the mitten. Lakes and rivers everywhere. Stay out of Detroit and Ann Arbor areas.
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When paddling in October in leaf peeping season, lake temps are usually still in the mid-50s to low-60s depending on lake location and elevation. The nights get cold when camping, and you can get frost, but I love seeing the fog over a still lake in the crisp morning air, hearing the wildlife wake up and get going, seeing the afternoon sun on the trees, etc. It’s the prettiest time of year to be on the water and it’s not crowded.
Still - it’s basically a 4-month paddling season for the non-hardcore. You do have to enjoy winter activities too.
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I grew up on Lake Champlain in the small town of Chazy, just north of Plattsburg.
The Summers were great (July and August). The other three seasons got hard on me as I got older. Almost Winter, Winter, Still Winter. 
If you can find something that you like to do in the winter then it would be a great place to live. My Grandson lives there and loves it. He paddles in the Adirondacks often.
I moved to south west Florida and paddle year round (except during the hurricanes).
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Agreed. Sept. - Oct are usually great. Black flies are mostly gone by Mid July in the northern ADKs - besides, the little beggars lay eggs in running water only, so they’re less bothersome in lakes vs. rivers.
BTW @Kevin777, I know Chazy, but never knew anyone who grew up there. Now I do!
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I think you need to be a migratory waterbird and have a winter and summer residence. Pitch your dwelling standard simply enough to be affordable.
My choices would be UP Michigan summer, ACE Basin SC winter(lots of tidal paddling- not ocean). Both have less expensive communities.