I grew up in Beverly, on the south side of Chicago, and moved to Lakeview when I was 18.

I moved from Chicago to San Francisco (I lived at 7th and Folsom), and then back again, regretting only that I hadn't moved back sooner. Then a company I started got funded and I got hauled back to San Francisco (this time in Noe Valley), where I stayed for another couple years, before moving back to the midwest (Ann Arbor), regretting only that I put up with San Francisco for as long as I did. We lived in Ann Arbor for 4 years before moving back to Chicago and putting down roots.

I had vastly bigger problems with crime in San Francisco than I did in Chicago.

I've only heard about the public school problems in San Francisco; my kids public school here has extraordinarily well-compensated teachers who ran a pretty competent college-prep playbook that got both of my kids into hardcore STEM majors (the boy's a biochemist now, the girl is out in Utah doing geology field work).

The weather was literally the first thing I missed about Chicago.

I don't know what "culture" means to you, but one of the first things I noticed about SFBA was that none of the touring bands I followed ever played there (a track record of closing every music venue in the city for like a decade couldn't have helped, a story you'll find well told at Jamie Zawinski's blog), and last call at the bars was, like, 11PM. Does culture mean museums? Check. Public art and architecture? Check. A theater scene? Check.

I'm sure Colorado is lovely and don't begrudge you your preferences. I don't think it's at all true that if you "ask any former Chicagoan" you're going to get agreement on all these points, or even most of them. If you'd said you grew up in Evanston and then lived in Kenwood, or Humboldt Park, the violent crime thing would be easier to take seriously --- but you lived in Evanston and Lakeview, which means that as far as violent crime exposure goes, you might as well have lived in Glenview. Chicago has a violent crime problem, but it's a deeply racist violent crime problem (not just demographically, with crime endemic to regions of the city that were de jure segregated until the 1970s, but literally racially: violent crime will follow you across the city border into the suburbs, but only if you're Black and have Black friends on the other side of the border).

I'm a startup operator in Chicago, and we do not have a good startup scene. Don't let me be taken as saying there's no tradeoffs to being here. You don't come to Chicago because it's going to be a game-changing win for your startup.