Success will be based on a large part, on how successful the club is at talent retention. We were able to keep the best player that the team's had since Barry Bonds only when he was willing to sign a very team-friendly extension. Even then, the Pirates never had any intention of fulfilling that entire contract. I remember how critical fans and Coonelly were when the Marlins backloaded Stanton's contract. We did the exact same thing, only with far fewer dollars.
I don't know who the first player is going to be to sign an extension. But, it's going to take a lot more than just one for the team to make the jump again.
I don't think talent retention is a realistic option. What good player would want to stay when he could leave? Not unless the Pirates significantly overpaid and that won't happen. The plan seems to be to obtain talent in the minors at each level to keep feeding the MLB roster for a period of years since good players will be leaving. Keeping their good players would be a much better plan. But Nutting won't overpay and there's no other reason for those players to stay if they have a chance to get away and spend a good portion of their career with a better organization.
It seems to me that BC realizes this and is trying to improve the team much as possible via trades for prospects with the understanding that Nutting won't pay to keep or obtain talent so there's no other way. It's far from ideal and not what I or other fans would prefer. But these are the Pirates.
Your last graph is spot on. You have to wonder what type of bs Nutting gave Cherrington regarding resources and when the time comes to up them. You also have to wonder why BC trusts Bob and even more, why on earth he took this job if that is the gameplay from here on out - which I don't disagree with your thought process at all.