"....but to be taking first cut of now throws up some red flags."

That thought crossed my mind as well.  However,  Upstate didn't really say it was being harvested now.  He just asked what a bale weighs.  It occurred to me that he might be buying this hay out of storage.  So, it might be good for Upstate to clarify, as it could come across a bit confusing.

Upstate, if/when you buy this hay, you might want to invest in a forage analysis.  I would even consider getting a forage analysis before I buy - that would give a better idea of what kind of quality you are buying.