You definitely can't take a chance with him, that's for sure. otherwise is just as well off as how you found him. if he gets out, he could so easily get hit by a car, attacked by a mean dog, or taken in by a kindly stranger who finds him. for the better part of an evening, you and your boyfriend could hang out outside with the dogs and keep an eye on them. if you go inside for anything, you'll have to crate him in the garage. it's not cruel. he may whine for a bit, but then he'll finally just go to sleep. keeping him safe and protected in his crate is definitely more suitable than leaving him outside in a yard that is so easy for him to escape from, so don't let yourself feel bad about crating him.