help!! how to make long distance work? and boyfriend's overprotective parents?

hey guys! so my boyfriend and i have been dating for five months, and we don't go to the same highschool, but we video chat and text every night and we occasionally go on dates, as much as we can. 
he's a junior and i'm a freshman, and our parents know we're dating but he doesn't want to ask his mom to take him places and gets awkward when we talk about family things. i wanna ask how much his parents know about me or if his friends can't drive him to dates what he would do but idk what his reaction will be! how do i approach this?
and also, the other day he mentioned college and how he'll most likely be a goner because he wants better for me but he said he wants to try to make long distance work from his college (he wants to go somewhere 2 hours away). do you have any tips on making this highschool college relatilnship work? we really don't want to break up.