I would guess that their excuse for the weird billing cycle is that they only order as much stock as they need to so they need to have the boxes paid for well in advance.
Services like that always seem off to me though. I don't like the idea of not knowing exactly what I'm paying for. I guess the gamble is kind of fun though.
It isn't really. It's just not fun. But it's not fun to try product after product hoping that you find stuff that's good. A good subscription box tries to make sure you get good things and you always feel like you're getting more than you paid for. This one...ehh...amateur hour.
My guess was that they actually used the money from the orders to help pay for the products in the box. They need to work on trying to get them out faster and make it seem like more value though. Maybe getting more samples from companies. Or even just coupons from companies.