Coming back to this now that I'm not on the road, if the Cubs had an elite closer I'd be fine with cashing in on that value given bullpen volatility, but they don't. Burnes they waited til he was on the cusp of free agency after multiple years of rumors.
But to bring this back to the Cubs, I would group these possibilities into 2 different buckets. One bucket is the players who are clearly above the '2-win whatever' standard and are the types of players you are likely to simply hemorrhage value by trading. Steele and Hoerner are in this boat primarily, and while I'm willing to admit there's a narrow path to a Bellinger trade working out, I simply don't think he will have any reasonable trade value so we should prefer to bet on his demonstrated ceiling and the possibility he doesn't opt out.
The other bucket is players who are good and not overpaid, but have a high enough dollar amount that they will not have significant trade value without eating significant money(specifically *future seasons money*), which eliminates a big part of the point of trading them to begin with. The idea of trading Taillon, Happ, or Suzuki will outstrip the reality. I also don't find it compelling that simply clearing the money puts you on a path to being better. Freeing up money while creating additional holes is generally a video game mindset that doesn't work out, as it requires unrealistic hit rates from prospects and in free agency.
Beyond this group though, I don't have a problem not being precious with trading players, especially given that the positional and offensive balance isn't particularly fine tuned at the moment. Morel, Tauchman, Amaya, Assad, Wicks, even Brown or PCA in the right move I can get behind, to say nothing of the positional prospect group in the high minors.