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He doesn't look too bad to me for a childhood pony who has endured years of love xD. I think he's just taken the battle scars of living with a kid, but those flaws make childhood ponies more precious (at least I think so, at least he doesn't have hoof splits! Two of my childhood mountain boy ponies have had glue surgery on their hooves for that particularly nasty condition.)
LOL, maybe! It does make him look kinda tough-guy. I did a Google Image search for Wigwam and a lot of them do look kind of thin haired... though not all seem as thin as mine. But a wash/condition treatment will certainly improve his hair situation regardless of how thin it is I'm sure...
(We were not super rough on our ponies for the most part... though our one and only Princess pony's bush-wooly companion got left in the garage and was smooshed flat as a pancake by the minivan! I probably should try to replace him someday...)
Lovely big brother! I have Chief with a forelock trim...(he was my brother's pony..hehe and the only boy in my herd.) That doesn't look like mold to me either.. I wonder if the reason he has the thin hair is because of the headdress accessory..? hmm! Anyway, if I were you, I would just give him a good external bath with warm water and a magic eraser and leave his hair alone. The internal bath and rehair would be good for peace of mind / if you wanted to do that (take his head off). It's weird how when cleaning ponies you discover stuff on them that you never saw before. I would be freaking out too..so don't feel like you're the only one! I am also in the middle of cleaning my childhood collection.. it's a stressful stress-free time..lol. Most of mine got a bath in the mid 2000s, never touched again until here recently. I'm sure the ones I lost would have ended up in the worst shape because I took them everywhere with me, which is why they are lost to begin with...