When healthy, our lines will probably look something like this:
McCann-Crosby-X
Kahun-Malkin-Rust
Simon-Bjugstad-Hornqvist
ZAR-Blueger-Tanev
Although I want to see how Chucky progresses, I think the Pens will definitely move him out. It just seems inevitable.
Adding a RW makes sense since we have much more LW type players than RW. I do not see GMJR wanting to depart with his 1st nor any of his high-end prospects. I can see 2nds or lower being in play and some possible prospects, as well as Chucky (who would get flipped for another pick by the acquiring team).
In all honesty, Rakell, Palmieri, Strome, Labanc and Kapanen would all cost quite a lot. These 5 seem like the really high end buys. A deal with Toronto would probably have to include a backup in DeSmith and a defenseman like Schultz with an extension attached to the deal.
Toffoli, Granlund, Smith, Fast and Pageau would all be considered "rentals", although resigning would remain a possibility. However, their respective teams will probably want to get higher picks for them.
Finally, Coleman and Kase's values are kind of in the air. Their teams can demand a lot, but they aren't guys you'd see a team giving up an arm and a leg for.
In my opinion, if we could get any of those rentals for a 2nd, Chucky and another "not too crazy" piece, I would do it. I do not think Fast would cost as much as the others. I also know that Pageau is a C, but I wonder if he could make it happen on the RW. I have always liked him and would love to see him on the Penguins.
I would also consider Kase if the price isn't too crazy. He has dealt with a few injuries, but a fresh start can be huge, especially playing alongside Sid.