1. Does it sound to you all like I have a supply issue?
(note: I have experienced engorgement and leaking. Have been able to
pump as much at 4oz at one time)
Not to me. Everything sounds normal. My daughter nursed every half an hour to an hour for the first month, and then went for an hour after that. She's only recently managed to bring it to three or more hours (although she's going through a growth spurt again, and now she's eating every two again)
Also remember that pumping is never a good indicator of supply, because babies are much better at getting the milk out than the pumps ever will be.
2. How can you tell if they are truly swallowing or just using you for comfort?
Listen and feel. Either way, I'd leave the baby there.
3. How on earth to you begin to try to get your little one on a schedule?
4. Is it too early to start establishing a nite-time routine? 10:30-11:00pm is pretty late for "bed time"
Seriously though. My daughter is almost five months, and while she has a rough "routine", she has nothing resembling a schedule. She is also a night owl, and tends to go to bed sometime between 12-1 AM.
As for your husband, you need to explain to him that breastmilk is SO good for the baby that it is digested very quickly. Breastfed babies have to eat almost twice as much as formula fed babies, because it just goes right through them!
I do feel your pain. It seems like it goes on forever (I literally wore one of the couch cushions flat we nursed so much) but it DOES get better. I finally relaxed and stopped watching the clock so much, and it really helped me feel better. Babies can't tell time, after all!
It sounds to me like you are doing great, feeding on demand, and meeting your baby's needs. You're doing awesome!