They Call Me 'MOM'

My roommate, T, and her friends, C and J, have always been there for me for emotional support since I met them first semester. There is one main problem, however, that has come to override the good in the friendship.

I have had to come to their rescue in a couple ways way too many times. I have loaned them way more money than most other people would even loan family members, I have had to 'babysit' them to make sure they are okay while they do illegal and/ or unsafe things, and I have had to go out of my way to cater to their needs more than I would normally expect to in a friendship.

I sold T a car for $3,200, of which she paid $1,000; I loaned her $200 for new tires because one of them popped while she was in Sacramento; and I have been covering her share of the insurance as well since she has not been able to afford it which totals $440. I have also paid $470 up front for T and C for a security deposit and their application fees for an apartment they were applying to get. J just owes me money for gas because he has been asking me to take him to work a lot. So in total:
T owes- $3,035
C owes- $235
J owes- $20

Up until about a month or so ago, I continued to let this happen because I felt like I should help them in each situation... like they had no other option and it seemed important. I also did it because I trust them to pay me back. Even though I still trust them to pay me back, and enjoy having them as friends, I realized that I need to start really holding them to their responsibility.

In order to do this and attempt resolving this very big, long-lasting conflict, I decided to take the car (which all three of them depended on) back since it is still in my name and under my insurance which I have been paying for anyway. My original plan was just to take it and sell it behind T's back without giving her a chance to explain or try to prove that she can afford it, and use what I sell the car for to just cancel her debt. So I have recently decided to just hold on to it until she gets her first paycheck, pays her first month's rent, and the deposit, then look at how much she will be making, and an expected budget including her rent, food, other bills, and see if she can still afford payments on the car, getting her own insurance, gas, and maintenance for the car. After explaining this to T, I made sure she clearly understood and agreed to these terms.

I think that was the better way to handle the conflict and still hold my ground; and either way I will get paid back for the debts owed to me.