Yeah, especially with the variable of pitcher health, and the Red Sox' own resources - I am less concerned about mortgaging 4-5 years from now. Am I concerned that the Sox have less ceiling in their org than they used to? Sure, especially without the same sort of monetary tools available to them (because of the recent CBA changes regarding amateurs). But their ability to solve that is on the scouting and development staff - and doing things like taking Jason Groome despite being a tough sign is a good omen there.
Dombrowski being aggressive trading guys he has not identified as future cornerstones does not bother me - providing we are getting the right guys back blah blah blah. The Red Sox will always have the resources to find worker bees. (and yes I recognize the luxury tax constraints - but that's John Henry's choice) And the stars they do have are so young that they will be heading into their primes in 3-4 years! Yes, the Sox might not be able to re-sign all of them, but that is fine. (Bradley for instance is clearly 3rd in priority among the outfielders)