My son is trying to get in UF fall of 2017. How hard is it to get into Windsor Hall? How soon should he apply?
Isn’t Windsor off-campus housing? I would email or call Trimark and ask when you can put down a deposit.
We looked in late February/early March and the single rooms were gone if I remember correctly. But there were still doubles/triples (??).
You should be OK if you check into it early this fall. They might not let you sign super early though.
The one thing we did not do is put down the $25 deposit for UF on-campus housing, mainly because I didn’t think my son would get in to UF. Trust me, that deposit is worth it!!! 
He did end up getting on-campus housing, mainly because he lucked out and found a roommate to pull him in.