Just realized I never updated this in case anyone else runs across my question. It turned out to be hen pecks from the girls and some rubbing on his food container that caused the spots and they cleared up after a few weeks.
I haven't noticed spots like this on any others so far. I'm going to take a close look at everyone this afternoon to check again. I should also probably mention he's the only Roo and the rest are hens.
All I've been able to do is treat for injury so far so I'm hoping that's all it is. I have no idea yet why he would be getting injured all of the sudden tho.
I noticed a spot appear on my Roo's comb a few days ago that I initially thought looked like a wound, but now I've found what looks to be a few small scabs on his comb and waddle. I was able to get a few good pics of his comb and waddle. Does this look like it could be Fowlpox or something...