[mykalberta]

In my past with friends $1000 one time per friend has been my "throw away" limit.

With gift/throw away money you have to be prepared that they wont spend it wisely and you have to be ok with that and not condescending about it. Just make sure you stick to your only $X amount and thats it.

You sort of know the quality of your friend after that so it can be a good thing, if in X years when they are back on their feet and you get an unexpected payback like I did from a friend you know they are stand up people. If you never hear about it again then you also know something about your friend which will allow you to judge your friendship better in the future.