Enticing package but I’d rather hold onto Dobson

You definitely should. Dobson on ELC will be extremely valuable until your bad contracts are off the books

Seeing the title of this post I was ready for something worse. It's not *bad* but like @AndrewLadd said I would rather keep Dobson. Isles are giving up a good lot of their D-Future for an extra 25-30 points Nylander brings to the table over Bailey.

Revise to: Dobson and somebody like Komarov (cap balance) for just Nylander. Keep your 2nd and Bracco (which is prob close to Bailey's value anyway so it evens out).

I'd like this a lot more as a Leaf fan if it didn't include Bailey's bad contract. Dobson looks really good, and I think hard times are coming for the Islanders, they have many bad contracts that are going to cause them problems in the near future. Having Dobson is vital for their future. As good as Nylander is, I don't see the Islanders doing this, although Lou is really not a good GM, so maybe he'll be part of the Parise trade that is coming this off season.

Bailey’s contract isn’t bad at all. 5 mil for a consistent 50 point scorer is market value more or less. I like the idea of pairing Bailey with Tavares in this scenario. They had excellent chemistry a couple seasons ago

It is 100% bad, 50 points doesn't cost 5+ million especially if you are at or over 50. Kapanen is more valuable than Bailey and makes less. Secondary guys like Bailey making 4.5+ are all bad deals. If they get the right linemates, they can produce more but on their own they are just average players.

you know who had excellent chemistry with John Tavares this season? William Nylander. He's also at the beginning of his productive peak and not the tail end of it. And a significantly better goal scorer