I'm in the process of selling my company and these weird dynamics are things that make me nervous.
Edit: in response to the negative comments and downvotes, of course I want to share the wealth. The problem is a lot of people (or at least a lot of my friends) don't like to feel like they can't stand on their own. Offering to pay for everything all the time is a turn off for a lot of people (on the receiving end).
The general rule I think is: don't gift something a friend can't repay with equal social value in their own way.
Or if you're going to anyway, make it explicit you're doing it for the experience, and don't make it a regular thing. (E.g. dinner at a very expensive restaurant you want to experience and you don't want to eat alone.) People know that rich people do rich people things, and "fun experience" is something that can be repaid without spending lots of money.
When there's a need I think in general whoever is best able to handle the situation should be expected to do so. This example is a bit extreme though because it's talking about nice gifts. If someone in the friend group had a car break down and couldn't afford a new one I would definitely think less of this person for not offering to help when they so easily could.
Not completely related - but this reminds me about things like parking tickets which disproportionately impact people with less money. If they're meant to be a deterrent then the fine should be some proportion of income, the $50 fine for one person needs to be a $50k fine for someone else to have the same level of impact.
Imagine not wanting to share trivial amounts of your wealth with your friends.
They are friends...right?
But just once he can't pay for a meal? I find it a little weird.
But again we are friends so it is what it is