After years of living in military quarters, I am quite familiar with the vagaries of heating and cooling. It's quite common for September and April to be no heat-no cool months to save energy. I survived with young children when there was no heat and the weather turned unseasonably cold. I'm sure there is a set date when the heat will come on. Then there will be complaints that some of the decks are too hot. They survive. DD spent her first sea term in the winter off the coast of Korea with no heat in her cabin. She slept piled with clothes and blankets and wearing a knit cap.
The winter clothes will be issued on whatever day was set to issue them. The supply officer is a M/N 1C who is up to his/her eyebrows in work that can't be dropped to change the issue date. True to form, DD had a complaint on this issue too. (She's a champion complainer!) It seems that when her company has formation at 0600 in the cold, the upperclassmen can't wear their cold weather gear because the plebes haven't been issued theirs and everyone has to have the same uniform.
I don't want to sound like I'm criticizing the parents who are concerned. I used to worry about similar things during DD's plebe year. But I've learned to just let go. It's a different world there, one that even after over 20 years as an Army wife I can't begin to understand. Yes, they're cold. It may be uncomfortable, but they'll survive worse in the next 4 years. Now, tighten that seatbelt because the roller coaster ride only gets wilder as you go on.