He seems much happier now that we put him in with the mares and foals. He still looks like crap but I've started feeding him before and after I ride like you suggested! Here are some pictures from yesterday!
Awww, sounds like a sweetie xD we have a Shetland gelding who is that way. He was gelded at 11 months so there's no way he was ever a daddy, but he seems to think all foals are his and that he needs to help raise them. Makes for the best uncle gelding ever when weaning time comes.
I agree, your boy looks lots better. If you can add that beet pulp in, I think you should be good to go!