1. They will try to contend in 2016. Some simple reasons here. First of all, the fans pay too much money to not expect a sincere attempt at contention. (this year was a sincere attempt - failed, but sincere) Second, the changes needed to get to reasonable contention are significant - but very much in the realm of possible.
2. As the last 2 months have shown, the everyday lineup is in good shape. Yeah you need to find a 1B you like ... the notion of lineup protection is basically bunk, but still the odds of Travis Shaw being anything more than Daniel Nava in terms of an "answer" is low. Ramirez could be an answer - or somebody else. But the team has significant ways forward at all of the positions - and will be above average in most of them (in terms of total package - I agree a corner bat in the outfield would be nice, not urgent but it'd help balance things), and have serious star capability in a couple. Even positions I have less faith in (hello, third base) isn't that bad.
3. Pitching staff needs a lot of work - at least one good starter, and basically reshuffling the bullpen. This is all true - but that's Dombrowski's job - and the team has a lot of prospects who HAVE to be moved soon. It sounds nice to build a cache of blocked starters like this is the reserve clause days. But as a practical matter, guys who get blocked will often go sideways or worse (hello Cecchini, Jesus Montero). Sometimes this is revelation of limited talent - sometimes it is just human nature (staying hungry, keeping your head up or whatever is cute until it looks like a promotion is flat out never going to happen). The Red Sox are bursting with middle of the diamond talent, among the hardest things to staff - and so moving that for significant big league return is a good idea.
4. Swihart's .680 OPS has to be looked at in terms of the shape of the production - considering how overwhelmed he was (and how overpromoted) he has settled in well. He was very bad for a couple of months and pretty darn good since. He's a baby. But the Red Sox have a surplus of catching - so moving one is a good use of resources in the right deal. So is moving Margot - who is probably going to be a Top 20 prospect in the next batch of rankings by folks who do that sort of thing - because the Red Sox have 7000 quality centrfielders including one right behind him (Benintendi) who has been the best performer of the Class of 2015 Draft so far (the entire class, not just Boston's).
5. One of Cherington's mistakes perhaps was - well not overvaluing the Boston prospects (the major league evidence is in his favor), but not being aggressive in moving the non-superstar sorts. Dombrowski won't do that. You look in the system, and Moncada, Espinoza, Devers, Benintendi (who can't be dealt anyway except as a PTBNL this offseason) have the sort of ceiling a team like Boston keeps, while the other guys are bulk to get major league stuff. There are some really good players in that bulk - our bulk is better than a lot of other teams - but now Dombrowski will probably take it for a walk more readily. The GM's job will be to make more.