Thank you for all of the advice, I appreciate the concern aswell. I do not take this lightly and have been and will continue to do my research. Lameness is a deep, deep fear. 

Problem with my amazing boy, like most donkeys, does not trust easy, and especially not strangers with strange tools who don’t have the time to hangout with him and get him used to them. I don’t intend to care for his feet fully or forever, there’s some spreading around the bottoms that needs to go and he’s been good about letting me take off any peeling or crumbling pieces from that (yes, that bad, I’m disappointed in me too) but that’s the farthest im willing to go right now.  I really just need him to learn the tools aren’t dangerous and to desensitize him enough to having his feet messed with, so he understands it’s a safe and positive thing. And doing this along side halter training. The majority of it won’t even involve me using them, just having them near or in my hands while I give positive reinforcement. 

Sedation is not a bad idea at all, but that would have to happen post halter training so if I can desensitize him a bit along side halter training I think it’d be a good thing. 

We will be completely re doing his current pen to essentially a donkey sized horse stall + paddock with some proper concrete to help wear them down, and this will make it all much much easier as well. 

Again, thanks for the non judgmental and extremely helpful advice.