OK, I'll bite. Congratulations on the new relationship. And that's the issue: it is quite a new relationship if I'm not mistaken! How well do you know the Favorite Bostonian? Well enough, apparently, to sell your home and follow him, with him doing all the business planning. Is this the Freebird that we know and love?
Now let's do a risk assessment. What's the worst that could happen?
1. You can't sell your house and are financially in the hole. The advantage of this scenario is that you have somewhere to return to if the romance fails.
2. You do sell your house, move to New England, and hate it. What are you going to do then?
3. You sell your house, move to New England, and break up with Mr. Boston after you find he is a money chasing swindler and has been diddling your finances. Nasty lawsuit ensues. You are now both poor and miserable.
4. You sell your house, move to New England, and are treated horribly by the Boston "family". You are miserable, but not poor, so at least you can make your own way.
My big worry would be #3. FGS keep your finances separate and manage them yourself.
You did asked for the tough challenges, eh?