It seems like everytime I give my dog extra time out of his crate, he has an accident. I would love to have him out of crate more often, but I just can't trust him. He is 6 months old now, and he can hold "it" when he is in his crate for 6 hours. However every time I have him out he will have an accident if I don't take him every 20-30min.

get a fenced in backyard take the crate there and THEN let him out .

you first of all need to pick him up right out of the crate and take him directly out. You also have to limit his water. you are not supposed to give water freely to puppies under a year because their bladders are not able to hold much and they are not able to regulate how much they drinkthey should get 1/4 cup every other hour even if they drink it up fast. At 6 mons they have changing bladders as welldon't give up