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I agree with you, although I think it would be really easy to go overboard here. Did you have people come to you asking for houses? Maybe I'm being cynical, but I think that news would spread really quickly if someone in my friend group was buying houses for several people.

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No, they kept it quiet. My close friend group is pretty distinct and tight so there wasn't really anyone on "the cusp".

That's probably a good clarification to make - some people have more friends than others so when you say you bought them each a house that could be just 4-5 people or 40-50. Good for you that you can share your good fortune with your friends without it affecting your relationship negatively.

No one has 40-50 close friends. Certainly not friends who you'd consider buying a house for.

Maybe I just have good friends but I feel like this fear is overblown.

I made a decent amount of money from a startup (enough to pay for a wedding + eventual retirement at a standard age). As part of this windfall I paid for a vacation for me and my close friends.

No one ever came asking for money. No one asked if we could do it again. Friends that didn't go have never asked for me to pay for their vacations. And if they did I would just say no.

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