I've had pretty mixed history with loaning money and getting paid back. A few times I've loaned huge amounts to friends--$50,000 for a bridge loan for friends who were refinancing their condo; $22,000 to another friend who was going through a divorce--and was paid back. I knew they were good for it when I loaned it. I loaned $20,000 to my sister when she was going through a divorce, and got paid back (after several years) when she sold her house. She gave me an extra $2000 in interest, which I appreciated.
(Much) smaller amounts I've loaned and never seen again, for friends/exes/family. Interestingly it's the small amounts--$1000 and under--that I usually never see again and frankly never expect to.
Currently, my down-and-out brother owes me about $9000 for consolidating and paying off his credit cards. It started at $12,000. I agreed to do it if a) he gave me all the passwords to his bank account/paypal, and b) let me set up automatic payments of $400 to be transferred to my bank account monthly. I also c) have an automatic email sent to him at the end of every month, about five days before the draw on his account reminding him to have money in the account for the transfer. So far, so good. I think what I've done with my brother is actually a really good way to do it. If they resent it or balk, well, they probably weren't sincere about paying you back. When I proposed these terms to my (big) brother he said, "Well, you're the adult here," which I thought was pretty funny.