20yrs of no playoffs - not even september playoff races - makes one appreciate a playoff team.
besides, who cares about payroll committments to older players in later years when we're just going to sign crappy old vets every year with that "savings" anyways? especially when all those contracts will be done by the time the next core is ready to contend?
Your scenario includes at least $76.5 million in commitments during the 2019 season to four players who have been worth a combined 6.8 fWAR in 2017. They've all shown some signs of decline in the last year or two, and at that point they'll be between 33 and 36 years old.
Can you afford to even
consider a Donaldson extension in that scenario? $100 million+ for five players over 33? With a third year arb salary to Stroman and second year for Sanchez, Osuna, Pillar, Travis, etc.? You're up around $150 million while missing three starters, a couple position players, a bench, and a bullpen, and most of that $150 million is going to players who project to be well below league average at that point. Yes, things would mostly start to clear up after 2019, but dear god that 2019 season would be a disaster.
I'm comfortable with the direction the team is heading. I think they're in a position where they can look at a Donaldson extension (along with Sanchez and Stroman) and see how they fit with the future core because, while they have two expensive players going forward, they can work around them fairly easily (as opposed to having 4+ expensive players who are nowhere close to living up to their salary).