As a young person in their early 20s, I think it makes sense for him to try his luck in NYC or SF and live that life for a while when his skills are in demand there. Once he's ready to settle down, move somewhere more friendly to that way of life. Better to do it now than regret not doing it later.
Austin, Boston, Boulder, Seattle, or Portland are all towns where one can settle down and raise a family without having to settle for a corporate 9-5 gig since there's vibrant startup/tech communities in these cities too. The option is always there and is especially attractive once you've got the Bay Area or NYC experience under your belt.
Austin, Boston, Boulder, Seattle, or Portland are all towns where one can settle down and raise a family without having to settle for a corporate 9-5 gig since there's vibrant startup/tech communities in these cities too. The option is always there and is especially attractive once you've got the Bay Area or NYC experience under your belt.