Johnhef:
My rule (Developed over MANY tries and failures!
) is this: Lend once, wait for repayment, then it's OK to lend again, but never more than you can afford to do without.
I've done EXACTLY what you're doing now...getting out of it will be as messy as you want or as he wants to make it. Please, consult some "learned friends" in how to procede in getting him out of the apartment. Your state/county/city may have laws that will bind you up for 6 months or better when getting rid of the deadbeat if you go about it the wrong way. Look for enlightenment from your renting peers.
Outside of that, your reputation as a "soft touch" may get mangled in the process, but in the end, you may someday need all this cash you're giving away for others in a better need than what's happening right now.
Good luck.
Truckinit:
Life's too short (As I'm sure you've been thinking about lately!) to let some bone-head take advantage of you when you were at your most vulnerable. A true friend would have thought twice before even THINKING of "borrowing" money from you while you were going through what you were. This person is/was no friend. Get legal advise, then sue (small claims - whatever) to get the cash back or a judgement (don't go after a lien) - consider the "friendship" dead - he did when he first approached you during your time of need. And he continues to demonstrate his nature by the lack of action on his part.
And when (or if) he starts paying you back? You can bet he'll be bad-mouthing you behind your back when he is writing out a check to you.
Drop him. You know, already, that he dropped you first.
Good luck and I wish/hope that things get better for you and your departed fiancee's family.
.