Here’s a simple rule-of-thumb for knowing if you’re being too generous with someone: if you taking away your generosity would anger them, you should.
Families are the poster children for this pathology. How many parents have indulged their spoiled children because they didn’t want their kid to be upset with them? How many extended family members have exploited the generosity of a brother, sister, cousin, aunt, uncle, or grandparent by playing the guilt card and asking for a handout?
If kicking your lazy-ass twenty-something kid out because they’re a bum means that you “alienate” them, then that means you should definitely do it. If they get upset, it only means that they view your generosity as something they deserve.
And there are few things more disgusting than entitlement.