The Stanford Newborn Nursery's website has good information on expressing milk by hand if you find that you're dealing with engorgement.
http://newborns.stanford.edu/Breastfeeding/
At that age, I was employed and living on my own. I'd make sure the guy knows that your family is there if he needs someone to eat dinner with but try not to worry about it.
Yikes. I can't see that working with daily visitation, not long-term. Does he currently live close to you and is looking at moving farther away? If that's what he decides to do, that might change what makes sense for visitation.
If you want one, there might be a doula in your area who would attend your birth, even if you choose not to hire a midwife. I don't know where upstate you are, but www.cnydoulaconnection.com is a great group.