You're doing good! Getting him acclimated to the bag was the same idea I had before our Thanksgiving trip.
I had Kaji sleep in it at night. I didn't zip it up or anything like that. Kaji is use to sleeping in my bed with me and what I did was have the bag up on the bed, put a blankie of his in it wrapped him in another like a baby and put him in the bag. I didn't force him to sleep in it all night, he was free to get out whenever. After a few nights Kaji slept in it for a few hours instead of staying in for 20 mins. I took the bag with us to our walks to the park. The park is 2 blocks away and I would carry him in it, zipped up with the flaps up so he can see. Once in the park I would let him out and whenever I thought he was tired, back in the bag he went! The only difference was it was unzipped so he can poke his head out or hide it if he felt scared, which with my shy boy it often. Just a thought. I hope this helps.