The short answer is, "yes, I did choose where to live based on my love of old houses." Some of what's below is based on our personal experience, and the latter is thoughts based on what others have suggested.
When we met, I had warned my now spouse early on that I planned to "retire" to Massachusetts. With him being a Florida born, this was important to point out because I was dead set on my plan and I knew he wasn't terribly fond of snow and ice. He already knew I loved old houses and living in them, though he likes to say he just likes "interesting" houses. Age isn't a definite factor for him.
After a few "follow the work" moves, and then a retreat to stay with family in NJ when work was hard to come by, he found himself working for the USPS and I was property managing. His job gave us some leeway when we realized we weren't getting any younger, so why not make the leap to MA then? The trouble was...
where in MA? Although we've lived in other expensive states, we still didn't want to put ourselves in a hole we'd never be able to dig up from, as it were.
I had a blessing of serendipity. When I got tired of looking at maps and MA forums one day, I went to look up the Gardner Museum I used to haunt when I lived in the Greater Boston Area. One of the results that popped up was not the Isabella Stewart Gardner Museum, but a museum in a small city called Gardner in north central MA. Amused by this, I did some poking about, found a lot of 1900-1950 homes on Zillow there, as well as a few other amenities that satisfied my mister's need to not be too rural. Out of nowhere, a possible place emerged.
He looked into open positions in the area, and we did a few day trips to suss out Gardner, other nearby areas, and look for rentals. (I should point out these "day" trips were 5+ hours each way that we fit in when we could.) Our plan was to rent first, which would make for an easier home buying search. He managed to get a lateral transfer, and I almost got a job myself (they wanted me to start sooner than I could.) We made the leap anyway, figuring I could always find something later.
Our home search was an interesting one (and well documented
here). One thing that really helped us out was we had not owned before, and I found a local first time home buyers program that helped us through the process--especially since we knew no one here before moving and had no close by "help".
In the end, our finding Beebe was a lot of luck and good timing. There were some points where we thought things weren't going to work out, but Fortune smiled up these two fools, and we've managed to weather those times.
If you plan to use your home as a B&B, you really need to do more research beyond the usual home purchase. If you've never run a business before, you may be shocked to find out how complicated and expensive some cities and towns make running any business (especially well established touristy areas). There are lots of variables to consider. (Also check if a town has explicitly banned Air B'nB style rentals.)
If your next purchase after the move is meant to be your forever home, will you find yourself buying bigger than you need just so you can have those extra rooms to rent? Will you have to pave over that nice garden on the east side of the house to provide code required parking? Do you plan to always rent right up until you go out feet first for the last time, or do you want to retire at some point before that, ending up with way more home than you can maintain? There are loads of stories out there promoting the Bn'B model, but that doesn't mean it's really good for everyone. It just makes for quaint photo spreads and heart warming stories about how folks finally are living their dreams.
I don't know what you do for a living now, but is there a different business you could run from your home (not necessarily a gig online) instead of hoping for rentals? Maybe there's something you always wanted to learn how to do like piano tuning (or giving lessons if you play), or being a locksmith. You might also consider things like running a small garden designer or home organizer business, even maybe do tax preparation work.
As someone who has made the long distance leap in part due to her love of old homes, I wish you the best with whatever you decide.