This is a really great point, and one that doesn't get talked about enough.
Yes, OTT has better pieces to sell than us, but their owner is a ****ing cheapskate. The odds of them taking back a bad contract is slim to none.
On the other hand, our pieces are still very good, AND we have space to take back a couple bad contracts. I think we'll definitely be the easier team to deal with come deadline day.
It's tough, though. OTT still has the best pieces to sell, and no GM wants to be the first to pull the trigger and overpay. Also factor in that you have some notoriously stingy GMs that have been rumored to be buyers (WPG, DAL, CBJ), and I could see this really going down to the wire.
Rangers have advantages, they have cap space for the rest of this season next and even the one beyond that before the 2nd contracts really start to kick in.
They have contract and retention slots open.
They have tons of real money and are not afraid to spend it.
They have like 12 players who all are going to be UFAs over the next three off-seasons. Some are obviously not going, some maybe they feel safer in retaining until closer to their contract ends, yet there are others who likely are going to be seen as outgoing rentals instead of extensions in their last contract year. I don't really see much point in holding on to them if something can be worked out sooner.
If the market sucks, maybe try to change the market by offering stuff other teams are going to have trouble matching. Really it does not even have to be just the primary buyers concerning players who have a at least one year of term left, expand the market to teams who maybe are looking to be better next season and see current NHLers as a better options than the not in the NHL picks/prospects.
If the picks have to be pushed off maybe see about the Islander, Habs, Oilers 2020 1st round picks.
Mostly I just think creativity has to be applied given the Rangers needing more than stuff that is a total long shot to even make the NHL, 2nds and B prospects to me should be the bare minimum returns and only after every other avenue has been explored and closed off.