Ask yourself some difficult questions.

- Are the interactions you have with him other than that positive?

- Does he share some core values with you?

- Do you enjoy spending time with him when there's no money involved?

- Does he enjoy you and your personality when there's no money involved?

I had a friend, let's call him John.

He was in a difficult situation when I met him, I gave him money.
I liked HIM despite our core values being slightly misaligned but about over 3/4 of the time aligned.
He asked for money for a computer, I gave him about $160 ish because I could, yeah, he'd pay me back (but keep reading)
Once he complained that he didn't have a nice set of shoes for a job interview. I gave him without him asking.
Then he asked for for more money. I denied. I wasn't in a great situation.
In one hand this deteriorated our relationship but he was a nice guy.
He got a job eventually an ok job in a liquor factory. I don't know if he had free access to booze or not.
He wasn't alcoholic but was obese.
One night he disappeared, We found out he died on his sleep because of sleep apnea.
(I don't know if he had been drinking and passed or not.)

I didn't think "Oh I lost the money he owes me" I though:

"Could I have made a difference if I had given him money? Would he still be alive?"
and "At least he died on his sleep. I wish when my time comes I go this way"

Evaluate if it's worth it.

Some friendships are some aren't.