I see your dilemma and must commend you on discussing so honestly all of your thoughts and concerns that you have as a parent and everything you have been doing for your son.
It must be tough not making enough that you have to pick and choose between yourself and your son.
I would suggest that you let him get a part time job. You are thinking about the job situation as if it were some type of punishment or if your son would lose out some how if he worked.
It is really good for a young man his age to learn about responsibility and the value of money. He will get a lot of out of working he will even be better prepared for the college years.
He will also be able to socialise while at work, meet new people, etc...
I guess what you may want to start thinking about is where he could work for example at a mall he can definately see other kids probably some of his friends will also have jobs and they may run into each other etc...
Just make sure you both do something fun this summer together like go to the beach or a movie.
(Anyway, I say you get a second job if you want to start putting money away for your future, your new school goals and his. Maybe postpone this though till the fall when he is back in school).
As far as the dad....there may come a day when he realizes what he has not done for his child or he may never realizes but that is not your concern you keep doing the right thing....you will always know that you did the right thing for your child.
Are you getting any child support for your child??? You should. Just take him to family court and file for child support.
Also, as far as health insurance some states offer it to lower - mid income families see if you qualify.
If not go through a health insurance broker they put other people that are not insured into a group so that you can all get together and purchase health insurance cheaper.
Well, I hope I helped you some how. Thank you for sharing.