I share your love for "real" Cadillacs; what GM offers as Cadillacs today, 600 Hp or whatever, leave me cold. They have no soul...give me any classic Cadillac, unashamedly American, with over-the-top everything. I was recently in the market for a new luxury car. Having been an Olds/Buick guy for decades, I decided it was time to treat myself to my first Cadillac. What a disappointment...this life-long GM man bought a Lincoln Continental (since discontinued as well.) If I were in the market for a new car today, I can't honestly say that there is ANYTHING that would float my boat, at any price. Guess I'll look for a rest-mod!
In contrast to your feature car in the first picture in the post, I'm far more interested in that Monte Carlo coupe than the Cadillac, although I appreciate the Caddy, too.
I think that GM totally screwed up the chance to communicate the then-new for 1985 downsized and FWD cars were as big a revolution as the downsized 1977 era B- and C-bodies were at that time. This failure would eventually affect the subsequent cars in this line, up until the current day. The feature car was a nice piece of engineering and 30 years later are getting their day in the sun. It's about time, if you ask me.
GM took the "be more like Toyota" advice that was hurled at them in the wake of the 2009 restructuring that many of their cars no longer have quite the character that they once did. Many folks complain that current Cadillac cars don't have uniquely American characteristics they once did, but I would argue that the cars are more like contemporary Americans. More competent, more aware, (hopefully) less insular and better prepared for any conditions.
I know many here would deride something like the CT5 Blackwing, but that would be a car you could drop in any environment in the civilized world and it will dominate. I remember being in Germany in the late 70's and seeing then-current Cadillacs attempting to keep up with diesel Mercedes on the Autobahns. Even with 500 CID engines, it was difficult for them. A CT5 would have no issue with that today.