Yeah, obviously you want your FO to be smart enough to predict Kyle being probably washed up and move on accordingly (something they did really well with the rest of that core). Lot of other nuances at play there, his history and longevity with the club, potential budget uncertainty, a pretty thin overall pitching market in general to your point.
The one I keep going back to is Sonny Gray, who's been a pretty reliable 3+ win/150 inning guy for the last 5 years now. Obviously he's a mid 30s pitcher, but feel like he signed so early that no one was really that concerned about his name coming off the market. I remember being generally against just stacking 3ish win guys at $20+m a year, especially if they lock themselves into a position/rotation spot that blocks a Shaw/PCA/Horton/etc. But here we are three weeks in with three lingering injuries to Steele/Taillon/Seiya, plus Merryweather sapping the bullpen. Things would have, unfortunately, worked themselves out (if the money was even there in the first place).