At school, there are teachers in loco parentis. On church trips, there are church leaders in loco parentis. Being on "his own" during family vacations, and staying home at night "alone" at night is not teaching him how to be responsible and trust-worthy out in the real world. It's teaching him how to be responsible and trust-worthy staying by himself. You mentioned that you let him go out in the evenings, so basically you're letting him dip into the lake up to his ankles, and then when he moves into the dorm you'll essentially be throwing him into the deep end, instead of using a more gradual approach, i.e., up to the ankles, then the knees, then the waist, then the chest, then the deep water. Momvic5 talked about rationalizations, and my opinion is that is what asserting that letting him go out in the evenings is adequate preparation for the first semester as a freshman in a college where he stays in the dorms for weeks or months on end, without anyone in loco parentis ,is.
We disagree. It's that simple. I believe supervising while he has his "permit" and letting him go unsupervised once he has his "license" IS gradual. You keep switching analogies. I don't agree that I'm sending him from his ankles into the deep end. I believe I'm supervising as he wades in further each year and when he's ready to swim I'll let him go. I feel no need to send him on little unsupervised forays into the deep end to test if he makes it back in one piece. I'll be able to tell because I've watched him slowly work his way out there with the support of me cheering from the sidelines.

) most parents in our society do not even consider the possibility that their child (or his/her friends) is gay. Most everyone just assumes straight unless proven otherwise.