For me it is very simple: I do not see a plan. I see a holding pattern and an inexcusable cheapness in being willing to sacrifice playing time for a top prospect in favor of at-bats for journeymen like JT Riddle who offer little to no conceivable upside even as trade chips.
I don't disagree with a lot of what you are saying, but I would again just reiterate two things: 1) there isn't a lot to sell and 2) if you completely sell whatever you can, you better have clear options for getting back certain supplemental talent.
The overall organizational problem as I see it remains tied up with what I'd call Huntington's success given the farcical constraints placed on him by Nutting with a simultaneous imperative to win as many games as possible without even retooling. As a result, we have an ok amount of decent talent spread across various positions. This season, which I agree should just basically be written off, there is a combination of bad injury luck and underperformance basically across the board. Even in a hypothetical fully healthy year of 162 games and no pandemic, the team is still likely the worst in the division (though I can't help but add that I'd have liked to see the Reds fail on a more spectacular scale, once again).
This creates difficulties in terms of how you actually go forward. I think the only option, given the likely constraints that will still exist in a few years from Nutting if we get some luck with top prospects, is to do whatever you can to develop star talent internally. This is why Tucker should now be playing every day and why Hayes should have been up and playing every day as of two weeks ago.
The bad wrinkle, IMO, comes into play when you start to look at glue-type pieces, which we already have a number of and which I'd argue is the reason why in a normal season, we likely wouldn't find ourselves coming to close to a top-3 pick (even if we'd have a shot at say pick 7 or so again). We often hear the refrain about rebuilding and not chasing mediocrity, and I don't so much disagree as insist on a depressing fact: without any exception at all, the teams who were successful in stripping everything to the total screws and developing their own stars, when it came time to really enter their competitive window, spent free agency money on supplementary type players.
That doesn't even get into the big extensions eventually given to their own stars, nor does it consider the questionable futures that the Cubs, for example, and probably also the Astros, now face. My point in raising all of this is to suggest that there is not one path to winning in MLB that can be easily emulated by the Pirates, for a variety of reasons. I think a component of this path has to include some measure of caution about auctioning off a guy like Kuhl rather than investing in him.
But more importantly than anything else, IMO, is the fact that we are wasting developmental time of our best current chance at a cornerstone player in the upper minors. The situation is probably made more depressing because Keller's velocity ticked down and now he's hurt – a shitty year and a continued muddy future would probably be more stomach-able with Keller having a great campaign – but nothing changes the fact that, judged harshly from the perspective of what seems like the only viable option for this team, Shelton is failing to incorporate Tucker in favor of no-upside players and Cherington is failing to promote Hayes for reasons unknown, but I'd speculate largely due to service time manipulation.
I will admit to somewhat of a bending the stick approach. I'm fed up with the ongoing decisions, but if we either clear some house by Monday or pivot forcefully for the final 30 games, I may be willing to sing a slightly different tune. To put a fine point on it, barring injury and regardless of how the house is cleared (trades, DFA, whatever), there is no conceivable baseball reason whatsoever that the lineups for the final 30 or so games of the season should be without Hayes or Tucker in them a combined five or six times.