I reckon every club would be "looking" (make that wishing they could) at doing a deal like that but it is hard to believe that it will ever happen unless there are some extreme circumstances that forced it.
GWS is a prime candidate on a few fronts
1) It has three first round draft picks
2) It is probably looking for super top end talent. It already has a NEAFL side littered with mid-late first rounders that can't get a game
3) It has a huge Academy pool this year, including 4 kids in the AFL Academy squad and 2 kids that made AA as underage last year. Having picks littered through the first round means they are less likely to get value on Academy discounts.
Point 3 extrapolated - Lets's say GWS end up with picks 7 (Coll), 11 (GWS) and 15 (Geel). If a GWS kid received a bid with ANY pick between 4 and 15, GWS would be getting less of a discount than if they trade those picks out for later picks (a few of discount losses are marginal, admittedly). Not going to happen, but IF GWS could get enough points to cover picks 7, 11 & 15, by trading they could end up with pick #2 and 3 elite kids. Rather than 7, 11, 15 & a second rounder and a bunch of late picks they won't use on standard selections...
For the record if we sent our 2nd & 3rd rounders (assuming we finish #17 and before any compo picks), we would swap 20 & 38 for pick 11.... We paid a lot more than that for the Charlie pick last year.
BUT all this depends on where Academy kids are rated. So it's all on hold until that is known.