It's going to be an interesting offseason. Assuming that Joe is out (I, like everyone else, believe he will be, although I go back and forth over whether I like that), I lean toward promoting Loretta, primarily for the sake of the coaching staff. This team has already seen 3 hitting coaches and 3 pitching coaches in 3 years, and I don't think another total overhaul of the staff is going to help matters (it may have been part of the problem in the first place). Plus, I do like Hottovy. I liked him in his previous role a lot, too, but it's not like the Cubs can send him back to that job. So promote Loretta and, if he wants it, make David Ross the bench coach. I'm not wild about him as a manager right now because of his total lack in coaching experience of any kind, but I think he could do well in a bench coach role (and he could work closely with Contreras to improve defensively).
As far as guys who may get traded, there aren't many guys who I think will be off the table. Among the position players, I think Rizzo, Javy and Schwarber are the only position players I'm 100% certain the Cubs won't try to move. I doubt they get the kind of offer it would take to spur them to trade Bryant, but Rizzo and Javy are virtually untouchable, IMO. As for Schwarber, for all the faith the FO put into his potential, it would be extremely odd for them to trade him just as that faith is being rewarded.
Guys who I see being traded: Almora, one of Contreras and Caratini (kind of think it could wind up being Willy), Happ (his recent surge can't hurt his trade value). I think they'll be willing to eat a sizable chunk of Heyward's remaining salary in order to trade him, but I'm skeptical that they'll find a deal. I think they might look for a similar deal for Chatwood, given how well Mills has pitched (providing an alternative) and how well Chatwood has pitched (making him a possibly tradable piece).
Among the free agents to be, re-signing Castellanos needs to be the top priority. Beyond that, I'd like to see them try to keep Kintzler if they can get him on a deal a little cheaper than his current one; Strop on a low-cost, incentive-laden deal (I really think he still has gas in the tank and just needs an offseason to get fully healthy again). Same goes for Zobrist if he doesn't plan to retire. Let Hamels and Cishek walk. Maybe keep Lucroy depending on whether or not one of the younger catchers gets moved.
As far as other free agents, it doesn't sound like the budget will be expanded this offseason, so even with the money coming off the books from Morrow, Zobrist, and Hamels, I'd be shocked if they make a serious run at Gerrit Cole or Anthony Rendon. I think Howie Kendrick would be an affordable option who could provide some real value offensively with some positional flexibility (potentially freeing up Nico to spend more time in CF, if needed). That said, one really wild idea would be if the Cubs decided they want to go all in to get Cole or Strasburg, they could free up a little extra money by declining Quintana's $11.5M option. I don't think that'll happen, but in terms of getting creative to work with the current budget, that's one way to get it done.
