The big question IMO is to consider is where do we have depth you'd want to deal from?
- Infielders, obviously. We're 3.5 seasons from an infield spot opening up. That doesn't mean you absolutely clean house on minor league infielders, but it does means that anyone you keep needs to be a complement to the current group or have the juice in the bat to survive a move to the grass
- RHH bats in the upper levels seem ripe, both because of the volume and because of the knock on effects of the infield being locked down as mentioned above. There's probably not a world where all three of Shaw/Alcantara/Rojas all coexist on the same roster for instance, and you can easily see quality bench outcomes from some of the other second tier guys like Long, Triantos, and Trice
- Catcher attrition is a horsefeathers and none of them are making any money yet, so there's no urgency, but the org has some high quality catcher depth. Especially if they intend to re-sign Kelly (which, pending the particulars, I'd be very into)
- Outfielders, man the org is loaded with outfielders. Upper levels, lower levels, lefties, righties, speed/contact types and power/whiff types. Like Brett Bateman is an age appropriate CFer at AAA with a 118 wRC+ and he doesn't get talked about at all outside of this insular community of prospect sickos. Ditto Carter Trice
Take it all together, and it feels like Rojas, Alcantara, and Kepley are probably the most clear pieces of trade bait. Whoever the org views as the lesser of Mo/Ayers is pretty high up there too. They all (presumably) have good value, but a combo of their skillset, their proximity, and the depth at their positions make them ideal pieces to dangle in trade.
I'd probably try and use Kepley/Alcantara to try and snag a high-end rental (Gray?), Rojas/Kepley/Alcantara to try and snag someone with team control (Detmers?), and break out the Mo/Rojas/Kepley big guns if some blockbuster opportunity presented itself.
For smaller trades, relievers and such, I think you lead with trying to clear out the depth at Iowa. Triantos, Long, has Murray rebuilt his value, etc. I think, aside from Bateman (he might be an ideal compliment for Shaw/Alcantara) a lot of these guys have had their most reasonable paths to playing time in Chicago cut off.