I think it is part of the plan. No, they don't plan to ever suck, except for 2020, but, IMO, they target their financial efforts, only when they think they are close. The Ben era was very similar to this one, and it did help lead to a nice stretch, culminating in the fantastic 2018 ring year.
IMO, the hope was we could not look so bad while we built up the foundation to the point where Henry okays "the pounce." Theo pounced. DD pounced with the Price signing and Sale/Kimbrel trades. Maybe Bloom will- maybe Bloom's eventual replacement will. The question might be, when?