Wes, I had a similar situation many years ago - several house cats and a feral who would sit outside the cat flap clearly yearning to get in. He eventually screwed up his courage and charged the cat flap. The house cats screamed in protest, but he wasn't hurting any of them and they soon got used to him. It was three months before he let me stroke him! I called him Geronimo, got him neutered, and he stopped spraying (thankfully!) and lived with us for the next 12 years until he died. Quite good going since the vet said he was at least 8 when I took him to be neutered.
So yes, I think your Buddy should be fine - and once he's neutered he'll be much less inclined to fight. If he already enjoys the foot of the bed, that might suggest he once had a home - and that he really likes you!
