I have nothing much to add about trust funds since I'm not an accountant. Since I did work in a tax library for a large accounting firm, I am aware in Canadian tax law, that if structured properly, trust fund can help in the area of tax savings.

Aside from trust fund lockhold for you, it sounds like maybe some deeper issues that you notice in yourself..ie. better financial planning/spending?

As a rule, have never loaned out money to friends at all. Just prefer to keep the friendship clean and trouble-free. But I have loaned and been paid back by close family members. And I probably never will loan money to friends. My approach to help friend in need, is to offer my place to stay for a few days. It hasn't happened yet, but that would be my tendency-- place to sleep, some food and a friendly ear to listen.