I do two cuts a year on my field in the Midwest. Getting hay out of the field is cheapest, followed by they deliver a wagon, followed by they get it out of the field, stack and store, then unstack and deliver. So as long as you anticipate the extra price you should be fine.
I have had people want me to store hay for them on my farm, and only pay for it when they need it, for the price I sell it out of the field.
Around here it can be harder to find farmers with the storage space to allow someone to pick up in the fall. I have gotten screaming good deals when a hay farmer calls me and says "I have 60 bales of alfalfa mix on a wagon that someone backed out of, if I can be there in 10 minutes you can have it for $5.75 a bale.
There’s always someone here in January who only has 1 bale of hay left in their barn complaining about the price or lack of hay.