I think that 95% of the time Jackson would be fine off leash. He minds well and listens pretty well. If I go to my cousins little league games, I will often just drop his 6ft leash as he sits there with us or lays down. When we go to my dads house for a night or two, I open my car door and let him run out because he goes directly into the house, and even if he didn't, there's nothing he can get into. My dad lives out in the 'country' and the closest main road is really really far away. One time a kid opened the door over there and he just came trotting out right to me, didn't bolt or anything.
But I've only let him off leash in a big unfenced areas on PURPOSE a few times. When he was younger, I did it a lot. We live on 3 acres with 90 acre farmfield behind us. My moms dog used to roam free all the time and Jackson would kind of follow her. Once she died, and he reached the age of one, he became more of a daredevil and on two occasions decided to go joy running and not listen to a WORD I said.
Anyways, like I said, I really think 95% of the time he'd be fine. But it makes me way too paranoid and nervous and I try to not purposely put him in that situation so he's on a 50ft line in situations like that usually. We had started working on recall a lot but lately I've been slacking and I really need to work on it again.