Lou said in the "availability" yesterday that he has conversations with other GMs every day and things are always being discussed (probably more than we can all imagine). I assume this is ditto for agents during UFA time. He also said they determine that most deals aren't worth what you have to give up to get the player. I assume by "deal" he also means potential UFA signings, factoring in all costs. I think we can assume with Lou that he factors into that how the deal could impact the team cohesion that he seems to value so much.
So, for example with Kadri, would it have been a good "deal", and I'm making some of this up, to "trade" Bailey, potentially a 1st or 2nd or 3rd round pick (if necessary to move Bailey), cap space of $2M for 2 years, plus the commitment of $7M for an additional 5 years, for Nazem Kadri? That's the way they view these things, and I think they only make a deal if they decide it would be a clear win (otherwise they'd rather not rock the boat for a minor upgrade). We don't know if they even were serious players for Kadri (or JG), but that kind of analysis is what they probably do to decide whether they make an offer to a UFA, and what kind of offer they make. So maybe they decided that they thought it was a "deal" worth making at an offer to Kadri of 5 years at $6.5M, and he declined. Again, making this up, but since we don't know anything anyway....
On the other hand, it sounds like the Romanov deal popped up last minute at the draft and they jumped at it. I'm sure they know the player, and they made the fast calculation that trading the #13 overall pick was worth it for that player, at his age, position and likely cap hit (in the short term, anyway).