I have no problem reading a long post like this one when it is well thought out and stated.
Like you, I believe the rotation is good with E-Rod likely to become a quality starter next year. I am not a fan of Buch but having him as a 6th starter is okay. I believe DD will not trade for a starter without getting equal or better value.
I also advocated the approach of not getting stuck on the idea of a full time DH but considering a DH from among our 25 man roster. Young looks like a potential candidate as does Swihart. Moving older players like Pedroia and Rameriz there to give them a break at times is also a good idea. I wouldn't rule out looking for a candidate that could play in the field and also DH part time. That wouldn't be EE. Again, DD should only go into the FA market to improve the team and stay away for long term expensive contracts for ageing player.
We may have a weakness at catcher next season, but all that talk is relative since there is no Johnny Bench out there. I am resigned to staying with the talent we have although who plays and how many make the roster is an interesting question.
I like our outfield and hope that jbj can make adjustments to his swing. We are solid defensively and if Beni can keep it going, I would take our outfield over any in baseball. Our infield is solid defensively but we still have a question mark at 3rd base. I don't like the idea of saying we should accept a position where we are weak because we are strong in other positions. If Shaw repeats his second half offensively and Sandoval is unable to return from his long hiatus, then we might have to rely on Holt and hope Moncada can progress rapidly. Justin Turner looks awfully good on paper, but he is probably unobtainable at any reasonable price. I don't know where else we go with this but think we could be weak throughout the season at 3rd.
Relief pitching is definitely needed with Uehara, Ziegler and Tazawa probably all gone. Abad probably won't be renewed either. I would look for one very solid setup man and another long reliever to supplement what Buch can give us (mostly in the BP).
We have seen some rather aggressive proposals for trading away many of our solid players, depth and prospects to get SP and RP. Some of those proposals seem like giveaways to me with less value and higher risk in return. DD is clever and I hope will not follow that approach.