What do you think about this?

Tell him he must find a job

Annoy him playing while he plays. Everytime he will be kicked in 5min and get a message to buy game.

I'd go and suggest piracy to him or maybe introduce him to Free to Play games on Steam. If he's a FPS freak, Planetside 2, TF2 or something.

Greedy bastard,if he has money he should buy it.
Don't give him shit.

Real friend or random who you have chatted to occasionally?

He's just greedy and selfish. I'd tell him it's "family sharing" you don't want to get banned if Steam finds out.

If he has to beg, then it's not family sharing. Just ignore and remove your permission for him to use your library.

Well, I wouldn't really share my library, even with my cousin. Maybe like brother/sister, but a friend def nos. He has money, if he wants games he can buy them. Don't mean to be mean, but that's how you got your games, should be his way too.

If he has funds to buy games, but still insists on begging for you to share your library then he is just a cheapskate and you shouldn't share at all.

Enable Steam Guard obviously!

It seems he might be a spoiled rich kid or something, seeing as you replied "he has money" when someone said "tell him to get a job". In any case, he doesn't seem to understand the value of money, or friendship.

Try having a little conversation with him about how videogame production is a business like any other, and if he wants to play games, and has money to spend on them, he should do so to support developers and encourage production of future titles. Explain how AAA games (which is most likely what he wants to play) can cost literally millions to produce, and a couple of hundred of peoples' effort over years.

Now, is your friendship with him a close one? Do you guys spend a lot of time together to begin with? Does he invest time and effort into the friendship / does he show he gives a damn about you as a person? If you're close, it makes sharing your library with him and him asking about it something far more understandable. If he doesn't really ever message you, or phone you, or help you when times are rough, but is still asking about sharing your library 90% of the time he does contact you, I'd drop him like the spoiled sack of shit he is. We call people like that "fair weather friends" - when times are good, and/or you have something they could use or want, they're there; but as soon as you need something, or don't have something they want, poof, they're gone. People like that are worthless to have as contacts, and don't deserve a jot of effort from you as a friend, nor you sharing anything with them.

1. share your library with him

2. Add games to wishlist

3. Wait 1 month

4. Guilt him into buying them for you

5. ???

6. Profit!

From your description of his behavior, he doesn't sound like a friend. A real friend thinks of how he can help you, not the other way 'round.

I think I like your avatar. Also, how close are you guys? If you're super close, sure, share that baby with him. If hes just some guys you kinda know, say no. If hes in the middle, tell him you'll share with him once he has something to share.