I can see where your comin from and how difficult everything must be.
But from my point of view, u have already been very supportive and loving to someone you havent been seeing for that long.
In my opinion, he needs to grow up. Sure there cant be reasons why you may have a hard time at jobs and stuff, but when ur employed and u hate ur job u should leave, not wait untill your fired.
He needs to start supporting himself than relying on his family so much, he has been working 5 years so should know how to take care of himself more.
In my opinion u have done more than your fair share. I can see why u wanna still be with him cos he may be a great guy, but he has really got to grow up a bit in respect to looking after himself.
If u do everything he will slowly rely on u more and more.
You are still at a stage when ur not totaly inseperable, so i reckon u should tell him ur on his side , but only if he starts to do things for himself
If you dont, then it will get worse
Also, u seem alot more keen on him than he does. You have a right to know where you stand so ask him that. Having a girlfreind doesnt mean u cant have freinds
I hope everything turns out ok.