My point is that pitching doesn't need to be traded for. Pitching can be bought in the off-season. If your position players are cost controlled (which they are right now) then you can afford to take on some inflated contracts without giving up young talent. If you trade young cost controlled hitters for pitchers with big contracts you are giving up both talent and money.
The Cubs have enough prospect depth in the minors that they don't need to trade away a cost controlled player has proven he can handle his own in the big leagues.
As far as position player depth, yes there is an abundance but not necessarily in the OF. If you move a Bryant or Baez to the OF their value diminishes IMO.
Buying quality free agent pitching is really expensive and you're usually paying for past performance. I don't think the Cubs want another massive pitching contract on their books like it would take to get Greinke or Price or Zimmerman. I think they will sign a middle/back end of the rotation free agent starter and target another front line starter through a trade. They wouldn't be trading for a huge contract, they would be trading for a younger, cost controlled pitcher.
The Cubs have a ton of OF depth in the minors right now too. Billy McKinney will probably be ready by the end of next year. Ian Happ, Mark Zagunis, Albert Almora are fairly close too with high upside guys like Eloy Jiminez and Eddy Julio Martinez further away. Also, like you mentioned Bryant could easily end up in the OF as well.