Im not sure thats the right approach if I was to even accept a reality where we are never going to be players for great players at market rate. Because if you think we have this guy who is just going to be awesome, and in 3 years hes going to be making 50m, so lets give him 30myr/7 yrs, only way we can keep him beyond the 3....But you are giving him such a raise in those first three years, where if you would just leave him cheap , its possible that you would have the resources to put a really good team around him.
So I think if we are being serious and seriously considering how we are going to be perpetually under funded vs some teams, then to compete with these teams despite having less, we should not look to take a smooth it out approach. And extend. I think if this were the case, and Im not saying it is, we may be better served by circling 3-5 year windows and building towards that. And if you are on teh eve of a 3 yr window and you ahve roman making 900k, it doesnt make much sense to extend him at that point vs keep him cheap and build around him.
Id rather take some years off to rebuild. I would rather build , play the youth, focus on the future, then flip a switch and focus on the present when that window comes, then stink again.
This is not your approach as you are always concerned about a contract being bad in its final years, but with my plan, if those final years are after your window closes , thats okay. So you can be more aggressive in the season in which you are actually going for it....And if you are trying to swing up, you may need that advantage.
Sucking in 2028, 2029 and being willing to suck in 2034, 2035 can be a big advantage to having a superstar team in 2031,2032,2033.....Because in 2031 FA, you arent scared to give a 6 yr deal to an aging player because thats your window. And in 2028, 2029 you can play your kids to see what they got.
But the redsox just try to be .500, third place, half win-half sell, balance, balance, balance....And I think this is why the results are what they are. Never above third place. First round playoff exit when you make it....