It's hard to know how he can or will handle trading prospects, since his track record is pretty much non existent, except for Aldo Ramirez for Schwarber.
His track record on big signings is not off to a good start.
If the prospects are not as good as we think, then trading as many as possible might work out well (kinda like DD trading away highly ranked prospects that mostly underperformed.)
If the prospects end up being good or very good, there will be plenty of "space to play them all," or we trade a couple here and there, once logjams are determined. Right now, we don't have any AAA prospects beating down the door at any position, let alone one already filled by a stud.
C: Teel can replace McGuire (trade RM)
1B: We have no top 1B prospect. Casas da man.
2B: We have room for the next MI prospect, here (or Story to 2B as Mayer plays SS)
SS: See Mayer to SS and Story to 2B.
3B: Devers forevers
OF: Plenty of room for Anthony & Bleis in a few years. Plenty of room for Rafaela and Abreu, now, and Dugo is gone after this year. Yoshida to DH opens an OF slot.
Pitching? We could use 8 and have about 2-3 promising pitchers who may be called up in 1-2 years.
There is room for one and all. (Only Yorke and Zanetello may end up being bottle-necked in the next 2-3 years, IMO.