He seems to have had quite a knack for living
off women.

It is easy. Just pick the "wounded bird" type woman.

Definitely not my style, but I have seen more than enough guys who were quite
willing to live that way. Surprising to me was that in some cases I might bump
into this one or that one only to find they had become "Born Agains" or were
now extremely hen-pecked husbands. Attoning for their perceived sins? Who
knows. In no case did I envy one for the woman he got.