I think it really depends on who you ask. However I think it's closer to the former than the latter.
To me, the "size" issue is just a microcosm of how the Rangers operate. There's always some gaping hole in the team, followed by some over-the-top move to address it which throws the entire thing out of whack and sends the team from one side of the spectrum to the other. The Rangers seem to be incapable of taking measured steps to address an issue. Instead they make a huge splash to address it and sacrifice in other areas. Sather is basically moving the same pile of dirt to different parts of the yard every year and saying he's trying to build a mountain.
And this goes back and back to what we've all known about Sather's tenure here, in that there is no fundamental philosophy to build upon. We had it in NY one year 2011/2012. It's no surprise that is the farthest we have gone under Sather. We had a team philosophy from the top down. Black and Blueshirts. Blew it up for Nash, and didn't re-sign Prust. All seemingly good moves, but when you go back to trying to build the mountain, it messes up the plan.
Then we didn't have enough depth to run Tortorella's black and blue system, so we trade Gaborik for further depth. Again, not necessarily a bad move.
However, we took it even further to firing the guy the team was built around, and bringing in AV to settle the pieces. Square pegs into round holes. Was it a bad move to fire Torts? Of course not.
Just because these are all seemingly good moves though, doesn't mean it's helping the big picture. It's a changing philosophy every year. That in itself is the biggest problem the Rangers have.
Now, this St. Louis trade, which seems to be the biggest argument of them all, is actually a trade I still agree with. It kills the Rangers in the draft pick situation, without a doubt, but it makes the on-ice product better. Are we seeing the dividends that we wanted yet? No, of course not. Is it fair to judge MSL after 7 games? I don't think so.
And, of course we didn't *have* to trade for MSL just because he wanted to come to New York. On the other hand, it was more and more apparent that Callahan was not coming back to the team next season. Sather, instead of choosing to lose Callahan for nothing, and deal other pieces for MSL, decided to wash his hands of the situation and let Callahan go early.
You say that MSL's trade value would have declined had we waited, but it surely wouldn't have declined enough to be had for the rights to Ryan Callahan, seeing as how it's doubtful enough that the Lightning will sign him on their own accord anyway.
So, let's say for fun that MSL didn't get traded to the Rangers at the deadline, but could instead be had at the 2014 draft. What would his value be? And now, who/what are we trading for him since we don't have Callahan as a proper trading piece?
/EndRamble