The SFBA B2C thing is not great in Chicago. IMO that's a retired man's game, but I thought bitcoin was dumb in 2010 so wtf do I know.
You'll do marginally better driving your own car if you catch that section of Guadalupe going south right at the perfect time when the lights slowly cascade to green as you approach Riverside.
(Course the tradeoff here in Chicago is looping the block endlessly looking for a parking spot, but in non pandemic times, I'd trade the CTA for CapMetro in a heartbeat)
And I even agree with you hear, now: I'd very likely move back for the same reason and if the council would stop caving to vocal minorities representing "neighborhood councils" who seem quite effective at derailing transportation planning.
I'm always surprised by how much tech. we have here now. So much more opportunity then back in 2000s..
If I had to rank U.S. metro areas in terms of favorability for tech, I would do:
Tier 1: Bay Area
Tier 2: NYC, Seattle, Boston
Tier 3: Research Triangle, Pittsburg, Chicago
Tier 4: Austin, Boulder, Portland, LA/Santa Monica, Ann Arbor
Tier 5: Everywhere else.
There's some industry-specific tech support in various other cities (eg. oil in Houston, automotive in Detroit), but in terms of a general tech industry, they don't really register.