Maile is not the one you'd be opening up a spot for, it's Jansen. Having Martin as a back up catcher is a waste. He can start somewhere else (on a contender) and doesn't have many more years left in him. Do him a favor and let him start somewhere else rather than back up 50 games on a rebuilding team. I think if enough money is eaten up he could bring back something useful.
Pillar is diminishing returns. He's not as good defensively as he used to be but is the same s***** hitter. Eventually that's not going to be a 2 war player, and I'd rather just move on now when maybe he has a tiny bit of value while putting Grichuk at CF. Plus, if Shatkins waited two weeks to call Alford up in Sept for super 2 reasons (as Davidi mentioned) then they probably have plans for him at CF reasonably soon as well.
Morales can probably be kept as a bench player, especially if they trade Smoak and hand the job to Tellez (having a vet to back up would be useful).
Tulo I don't expect to ever play for the Jays again, either due to injury or being let go, so this is a moot point.
It depends. Someone better in 2019 or someone better from 2019-2025? That's what we should be determining. If we trade Pillar and put Alford at CF (as an example), yeah, we probably lose a win or two in 2019 depending on how Alford does, but who cares? The objective would be to develop him for future seasons. Anything he gives in 2019 would be gravy. There are many layers to this, not just wins in versus wins out in 2019.
I never said pick up 2 Sp's or 2 Of's. Picking up one Sp is what I expect, and maybe one cheap gamble (Garrett Richards?). I only mentioned adding one OF as having Grichuk at CF, a new OF in one of the corners, Billy McUpton in the other, and Teoscar at DH is an option that is worth exploring if they choose to go that route.
Trading Martin, Smoak, and Pillar for something of reasonable value shouldn't be too difficult. Morales and Tulo will have to be dumped, which I don't expect to happen with Rogers owning the team, but who knows.
Shatkins made 8 trades at this past trade deadline. Moving a few more vets shouldn't be asking too much. It's not like I'm expecting top 10 prospects out of it.