Legal Question in Real Estate Law in Massachusetts

Well, you made a mistake purchasing the time-share - do not expect to get your money back (although, I note, that there are lawyers who sometimes sue these companies, as it is a heavily regulated industry - and you may contact one of them). The two of you should work together to sell it. Don't be petty. You had five good years together. You'll take a big loss on it. Better than than accruing years of "management fees" and getting sued as co-defendants.

If you cannot afford the house, you will have to sell it. When you say "I purchased the home," that suggests to me that it is solely yours - assuming that case, you should be able to sell it and keep any profits. If your house is now underwater, you can try for a loan modification, a short sale, or - maybe your best bet - get a roommate. You could also rent out the house completely, assuming you can cover your costs (although you need to talk to your insurance agent if you do this).

Try and understand: your creditors do not care about your personal life. So although you perhaps feel stressed and anxious, and a whole lot of feelings about your lost relationship - your bank is unaware of this, and just wants to be paid. If the house is in your name alone, I am not sure how you can sue your ex boyfriend for any money - unless he made some kind of promise to you, or unless you have children together. The good news is he probably has no claim to the house himself. Massachusetts does not recognize "common law" marriage.

In short - you should move on with your life. Don't get sucked into hoping for things. Maybe your relationship will be reinvigorated at some point. But if you keep the status quo, hoping he will move back in, and fall behind in your mortgage payments when he doesn't - you alone will suffer.