I had been a little scared to water him too much since he was sitting on the floor and I wasn't able to tell if there was too much water until it started to spill out from the bottom and I really don't want to mess up the floor. Now though I can simply roll it to the side and check. Of course I drilled holes in the base of the dolly so it wouldn't hold water in it. There is a divot in the middle of it.
After this I added water and no drips! So I added more water and still no drips. And added water. And added water. And so on. I think he was well under watered which would explain the slow growth compared to earlier.
I now have high hopes for him to start taking off again and look forward to many more leaves and hopefully height. There were decent roots in the soil when I transplanted him so I don't think there will be a problem. I've even already seen a new little leaf trying to form. I'll check every day for a while to make sure he's happy in his new pot.