yah, he lived on a trust fund for the first year. I've wondered why he thought it didn't apply to him. Perhaps, being a student then writer, work was never his inspiration, he had others.
Which ones? His earliest adolescent stories were buddy stories, eg Becalmed in Hell, Wait It Out. I can only think of inherited wealth in A Relic of the Empire (Rich Mann).
Been years since I read his early stuff, but as far as I remember, a lot of the early stories about teleporters (proto-Known-Space) featured youngish middle-class men in California with no apparent means of support.
I hadn't thought of it in terms of "no apparent means of support", but didn't pick up on that. There was Gil the ARM; a belter; and later Elephant (whose great^n grandmother invented the displacement booth - that qualifies!)
I feel I know the stories well, so it's disconcerting that maybe I missed something. I'll keep an eye out if I read them again.