Ok, here is a hypothetical and you can tell me if you'd be disappointed, and I'm going to go with czman's thoughts about CF this time around:
Soler and prospects in a deal for Shelby Miller
Castro and Hammel dealt in a 3 team deal where the Cubs get Ender Inciarte and a solid pitching prospect
Samardzija signed for 5/$75 mil
Heyward signed for 6/$150 mil with opt out after 4 years
So you'd be looking at this (you could probably lead off with Heyward instead if you wanted):
Inciarte (CF)
Bryant (3B)
Heyward (RF)
Rizzo (1B)
Schwarber (LF)
Montero (C)
Russel (SS)
pitcher
Baez (2B)
Rotation:
Arrieta
Lester
Miller
Samardzija
Hendricks
That team likely wins the NL Central and would certainly be favored. You will have improved contact rate in the batting order and your defense at RF, CF and 2B while getting Baez' HR potential in the lineup. The rotation would be one of the strongest in the NL. The net payroll increase over 2014 would be less than $20 million allowing flexibility at the deadline. You also wouldn't block Almora because Inciarte can play any OF position and with Coghlan gone in 2017 you'd have improved your flexibility there and decreased pressure on Almora. You can operate within budget constraints and improve your team for 2016 and going forward. That's a better team than if you stood pat and signed a CF and David Price which would cost about $5 to $10 million more in 2016 than my scenario.
Let's say you do the Hammel/Castro deal. Then let's say you go trade Montero to free up cash, then I'd go
Sign Heyward
Sign Zimmerman
Sign Lackey
Incarte - CF
Heyward - RF
Bryant - 3B
Rizzo - 1B
Schwarber - C
Soler - LF
Russell - SS
P
Baez/Coghlan - 2B
Arrieta
Lester
Zimmerman
Lackey
Hendricks
Why this route over your route: I'm not sure there's a place for Montero on this team at the salary he makes. He's making 14M but the Cubs at most probably are going to start him at most 100 games in 2016 (the plan is obviously Ross catches Lester then Schwarber is still going to get reps at C, especially to get a guy like Coghlan into the lineup). Obviously Contreras is a future part of that plan but he may even be ready for a call-up by some point in late 2016. Basically, Montero is a good player but when you're eating up close to 10% of the payroll, I'd like you to be more valuable than "starts 60% of the games and hits bottom third in the order".
My plan obviously calls for more starts for Schwarber/Ross but I'm not sure that's terrible if the money gets you a more "sure thing" in FA in Zimmerman and then you still have enough to get Lackey and Heyward. And while trading Soler makes sense to solve today's problem, there's still a chance you're trading a .280-20-90 guy for a #3 starter when you can simply sign a #3.
The way I look at is this:
I downgrade Montero for Schwarber defensively but get a better bat (Soler)
Soler is an upgrade defensively in LF over Schwarber, especially next to two top defensive outfielders
Lackey is probably close enough to Miller that trading Soler to get him doesn't make the deal worth it when you have freed up cash from trading Castro/Montero/Hammel
My opinion on Zimmerman vs Samardzija has been well stated