In the early 80's when he made Sharkey's Machine in Atlanta, he tried to launch a production studio there. He needed city cooperation - TIF financing or something - and they didn't go for it. He certainly had the right idea, but was about 30 years early.
I recall seeing City Heat - a not so well executed film with Burt and Clint. Assumed to be a guaranteed hit with those two, it underperformed. More importantly it was the downfall of Reynolds after he was injured in a fight sequence, causing a TMJ injury which led to pain medication addiction. Everything seemed to be downhill from there. I always found it interesting that at the time of that film Eastwood and Reynolds were on par as film stars, and afterwards Reynolds hit the skids and never did much of note. Eastwood honed the saw and became a fine director and acted in a number of successful films, and continues to direct to this day. What divergent paths.
Your right his career was never the same. He had a sort of comeback with that TV show “Evening Shade” but I never really liked it much. He ended up doing a lot crap, direct to video, etc. just to get a paycheck.
It’s shame that he did not manage his finances better than he did, probably was stolen from, given bad investments, etc. If he had just stuck to blue chips and bonds he would have been fine.