Nice pick ups in trade ... but meets limited needs, creates holes, and upgrades not needed.

CAL ... short term gain for long term sacrifice. Short term C solution and an older longer term winger, but we're deep at wing.
Backlund vs Hornqvist ... Both UFA at season end. Both likely to get bigger offers than the Pens are willing to give. 1yr players ... hole at Center for next year. Could be worth it.
Frolik vs Sheary ... Good player, no point. I'd just keep Sheary as production won't be any better, and I think his age opens up more trading partners.
And then the 1st ... I'd rather keep it then make this deal.

Trade: Backlund for Hornqvist with a late pick (4-7th) going either way or trading picks up or down picks (1st/2nd for a 2nd/3rd) ... but don't see a point for us to get Frolik, at his cap hit and term. Pens have depth at wing. If you're trying to sweeten the deal add a prospect or a pick instead of swapping players.

WPG ... You hurt D depth this year, band-aid it, take away future cap space (limiting depth), and opened up holes at goalie ... But get Lowry.
Trouba ... Do we need him with Letang and Schultz, Malkin playing point on the PP, and Pouliot (if nothing else he can put up points)? 2 NHL defenseman for Trouba ... band-aid the other spot (tells you it's a weak deal for a cup contender) and Trouba's next deal is going to be 2x as much as he's making ($5m + maybe NMC) so you lose cap space for filling all the other holes. Hopefully Pouliot works out or that's more moves that need to be made.
Lowry ... C/LW that helps replace Hornqvist's net front on PP, and RFA. Excellent depth that allows for other moves. RFA, likely to be affordable for a while.
Jarry ... might be a future NHL starter, meaning we could trade him for a lot more at seasons end or next season than we can now or keep him and have a 1A, 1B situation with him and Murray for a bit (worked out last year). What if he ends up being better than Murray? No point in trading him for luxuries. DeSmith can go.

Trade: Lowry and Trouba for Sheary, Maatta ... throw in some picks like mentioned above or a prospect. That's more a win/win, but does WPG want what we want to move?They might not be a good trading partner.

I like all the players you get, but feel like you're chasing things not needed (Frolik,Trouba) while giving up things more useful (depth and future).