I think this is bingo. Bradley as everyday CF sounds lousy, but if you get excellent bats in LF (Schwarber) and 2B (Kike), you've upgraded two positions to help pay the offensive bill.
That seems like it would downgrade the defense in three positions, though, as compared to a Verdugo-Kike-JBJ outfield with Arroyo at 2B, and IMO the Sox should be looking first to improve their defense.
In LF, Verdugo > Schwarber (who's not even on the team currently), and in RF, JBJ > Verdugo. Kike is much better defensively in CF than 2B, where I'd give Arroyo a chance at the job after an offseason getting healthy. If/when Arroyo gets Eastern Equine Encephalitis, then you can move Kike to 2B, or continue down the depth chart.
They have some pretty great flexibility at many positions now, which we know they value, and much of it is already on the field in the form of a starter at a different position. That might allow them to go with a shorter bench and keep the stronger, starter-quality players on the field more often, with enough flexibility throughout the roster to give everyone a break when they need one or fill in for minor injuries and not lose too much.
JBJ: RF, CF
Kike: CF, 2B, SS
Verdugo: LF, RF
Dalbec: 1B, 3B
JD: DH, LF (if needed or to keep him happy)
There's probably still room for Schwarber (1B, LF, DH): they need depth at 1B if he's willing to keep working at it in the offseason, he'd DH some, and play LF if they see JBJ on the bench more than I think they do.
Even with Schwarber, they'd have 6 primary players for 5 positions (JD/Schwarber/Dalbec/Verdugo/Kike/JBJ for DH/1B/LF/CF/RF). That seems reasonable, especially if you plan on Kike and Dalbec getting a fair number of games at positions not on the list above, as they did last year. The average is over 140 games per player.