Yes, I have a really awesome avian vet actually, who keeps chickens herself. I almost called her today, but I figure it will be easier for her to look at his feet when they aren't covered in dried blood. I may give her a call next week.
He has SO many new feathers that have been growing in during the last two weeks and most of them have grown in really quickly and no issues. So I was really thinking we were definitely on the way to no more problems. I was even able to let him out with the girls for a bit. I noticed a few days ago that this feather (the one that broke today) kinda looked odd and different from the rest of the nearby feathers. Like the blood in the feather shaft was not receding down.. not sure if that is making sense really, but it's hard to describe. The feather seemed to be fully grown in and the top was slowly peeling away as it unfurled, but the blood supply appeared to be still all the way almost to the top of the feather, rather than receding down as it would normally when they feather is done growing in. I have no idea if that even made sense. I am horrible at describing things. I wish I took a photo of it before it broke.
Even though this feather broke, it was definitely much stronger than the feathers he was losing in the beginning and does look almost like a normal feather but not 100%. Before the feathers were growing in with odd grooves and were so incredibly brittle. This one was not as strong as normal, but was definitely improved. Maybe he needs more time? I feel like this is such an odd problem.. I find myself really missing our family patriarch who started the family farm and kept 1000's of chickens through his lifetime. Any time I call the vet she jokes that if he was still around I'd never need to ask anyone for any advice other than him!
On another note I did find this article on west nile virus in birds (not in chickens though)..
http://owls-perch.blogspot.com/2012/09/q-corner-west-nile-virus-and-feathers.html And it seems to have oddly similar symptoms to what my boy is experiencing. That's something to bring up to my vet. Guess it's time for me to do some research on west nile. I always see on the news that they are finding wild birds positive for it in my area. And I also live on the edge of some wetlands. Thanks for all your help @Eggcessive I'll continue to update this thread.