How To Handle Son's 'paralysis Of Analysis'

So here’s the deal:  Ole single pops (38, not that old) is now, after almost 10 years, has his son with him again, full time.  Now, son is 19 (yes, I started early), just in 3 weeks ago from the city where his mother and her hub had moved to.  Trying to get financial aid squared away for him for school.  Hey, vets, you know Post-911 GI Bill, you can TRANSFER (unused portion) to your kids?  That’s what I’m trying to do.  Seeing if I can get up to 70% paid, then FAFSA for the rest, and since I don’t make a lot, he might see some more money.  Now if I can just manage his transition from boy to young man better.  Seems mom either hovered over him or let him do whatever (divorce guilt?).  Anyway, now it’s me who has to square him away… like not sleeping in till 11am, which is impossible to monitor since I’m at work.  Then I have to worry about him thinking how can I parent him when I haven’t been there, except in visits?  But I decided I would parent first, friends later.  Already had to put him in his place.  He doesn’t have to like, but sure as hell has to respect me.  I make sure he knows its because I love him, he is my son.  I think he knows.  Its hard to do, haven’t been a full time dad, in 12 years, coming off another soon to be divorce, starting over (she took almost everything).  Then there’s the strangeness surrounding his mother and I.  I hope he see’s the effort I’m putting in and see’s the value of work.  Seems kids from the city he’s from now just are so cynical, and can only comment on things without actually doing.  They read or watch stories but are too afraid to make their own stories.  Last week we watched Tropic Thunder and when he see’s the actor/soldiers flying in helicopters, its just a scene.  When I see it, it reminds me of being strapped in a Blackhawk with my buddies, buckled in, doors open and trying to feel like I’m breathing from the rotor wash.  When he see’s the huey’s fly up or down (nap of the earth), again, just a scene, but I FEEL my stomach and legs tense up, remember clinging to my M16 very hard, thinking ‘this pilot is certifiable’ and ‘helicopters can’t do that!’.  Just seems kids read and watch stories, play games, but suffer from some sort of ‘paralysis of analysis’ and just can’t or won’t get out there.  Anyway, does anyone else experience this with there now young men, young women kids?