In fact, this off season is one where I am glad not to be GM. (Like that was a tough bullet for me to dodge.)
The free agent the Sox need the most to really get back into contention quickly is Trevor Bauer. There might be a Perfect Storm brewing to make this possible with 1) per MLB Network talking heads on High Heat, there will be fewer teams actually spending money, a list that does not include the Red Sox, 2) the Sox are in desperate need of SP 3) the Sox have been very public about achieving their tax reset, which should be the green light to spend again, and 4) Bauer's personal hate-hate relationship with the Yankees' Gerrit Cole (which, at best, is a tie breaker in his decision-making process, if it enters at all.)
But the problem is, Bauer is very likely looking for a deal in the neighborhood or what David Price had, if not more. His goal might even to be a bigger contract than Cole, just because. This is a major step to putting the Sox right back in this type of mess we have today, especially since, so far, Bauer has simply not been as good of a pitcher as even Price was at the same ages. Bauer is still certainly a very, very good pitcher. But even Price had a much, much better track record (31.1 fWAR, 1 Cy Young award) entering free agency than Bauer (19.3 fWAR and counting)...