During the suburban expansion of the last century many southern CT towns allowed in businesses but declined to expand housing and transit availability. This combined with strong NIMBYism drove up housing prices in southern CT.
A good modern analogue of southern CT from the 70s-90s would be the valley in the bay area e.g. Palo Alto, Mountain View etc.
Not disagreeing with you but some additional points:
I don't think CT's housing issues are anywhere remotely as bad as the Bay area. Stamford is the tier 1 city in CT IMHO, which seemed kind of lame. i.e. we would have friends in places further east (almost as far as New Haven) who would come to Stamford for the "scene". I use quotes because the scene in Stamford was pretty muted. We (who lived in Stamford) would drive to Manhattan for our weekends and special weeknights. I thought it worked really well for us. For 2400 a month, we were living in Luxury apartments and life was car friendly. Housing didn't seem too overpriced (starter homes were 600K IIRC). IMO, Stamford was pretty neat a few years back .. not sure if it has changed.
Bay area housing just went stupid until the pandemic hit. I moved out and so did many people I know. It was just not "affordable" on a 200K salary if you have multiple kids and a stay at home spouse. The housing you could get for $2400 was terrible in most parts that were reasonable commuting distance. I also would take metro north over caltrain any day.
Taxes are bad in both places. Stamford seemed more affordable and a lot better culture to me. I love the Bay area but can't make the math work :(
A good modern analogue of southern CT from the 70s-90s would be the valley in the bay area e.g. Palo Alto, Mountain View etc.