K.V.
It sounds like he is ready, he's getting the idea if he's taking his clothes off to go. My daughter isn't quite two and I'm letting her run around without clothes right now and she often makes it to the potty. If she had any interest in working her own clothes I might not have gone this route. If I were you I'd definitely consider a potty chair in his room at night and tell him that if he needs to go potty he should take off his clothes just like the other day and sit on the potty to go. (They understand more than we give them credit for sometimes! I told my daughter tonight as I put her night time diaper on that diapers were not an excuse to go potty in her pants, just there in case of an accident and that if she needed to go she should tell mommy in time to get her clothes off and sit on the potty. Pretty soon she was out of her bed knocking on the door, when I came in to put her back to bed she told me "potty" and her diaper WAS wet!)