We practiced leading today and actually had some success at it! We got some straight lines going and he walked with me in and out of his stall a few times. Still not a 100%, but a definite step forward.
In our second session (in between I went and worked on digging ditches to try and convince the water to go away) we went for a walk outside again. Walking out through the gate was okay. Unfortunately it's gotten really mushy right outside the gate. We weren't having as much success walking alongside me when we were outside, he was getting a bit...opinionated. There, it works better if I hold the lead with my outside hand and am angled slightly towards him, and my inside hand has the stick that can tap his rump, he'll walk forward this way sometimes when leading him "normally" isn't working very well.
I let him nibble some grass and then had an awful time getting his head back up, lol. The only time I had to loop the rope around his rump was to go back in his pen. He was being a bit uncooperative about going through the gate but it's so mushy there now because of the rain I didn't want him making it any worse so I just looped the rope around and said let's go and he hopped inside.
Probably one of the best things about today though was that I was able to walk up to him in his pen and pet him without him moving away and going in his stall! I did it once when I picked his pen clean before working with him, and then with the halter in hand, I walked up and was able to halter him without him walking away--both times I worked with him.
It's kind of fuzzy, camera was too close, but here is a silly picture of his front teeth. His two middle teeth look kind of odd, but you can't really see them very well. I'll try and get a better picture tomorrow. One nice thing though, top and bottom teeth appear to match up, no over- or under-bites :)