This is coming from a guy who typically thinks Sather has been awful during his tenure here...
You say the bolded above like being stingy on RFAs is a bad thing... This should be what you want out of a GM. You want your GM to make the best use out of the cap space you have; and keeping players' contracts down allows you to attempt to do that (of course, ******** that space away on big ticket FAs nullifies that, but that is not what is being discussed here).
Unusually, I have no major issues with Glen's offseason this year -- especially as far as Stepan is concerned. I agree that his future looks promising, but a lot of people around here are acting like he is a lock for 1C indefinitely and deserves to be paid as such. Sorry, I don't buy it. He has been on an upward trajectory, but one stellar half season in a contract year does not a 1C make. It means he still has something yet to prove before he gets paid; if he replicates the same performance this season then I'll buy in. But until that happens, to me, that means you move forward with cautious optimism. And this is why a couple year bridge deal at slightly less $$ fits his situation perfectly.
The idea that Glen hasn't prioritized Stepan because he made other depth signings first seems like a reach to me. He is often a bumbling fool -- and I think there are many things he does poorly -- but I find it hard to believe that he (or NYR's cap management staff) can't do the basic math to figure out how those signings impacted guys that were left unsigned.
By signing other RFAs / FAs before Stepan, Glen has taken away any minimal leverage Stepan or his agent had left. They can't even claim that Sather/NYR can afford it -- because he legitimately has no room left to give Stepan a larger contract than he seems to want to give him.
If that has been Sather's plan all along, and he has some sort of "out" lined up in the unlikely scenario that Stepan gets offer sheeted, then I don't see this as the awful GM decision that it seems some would make it out to be.