Easiest way to get on his good side: Don't struggle. It will go easier for you.
Easiest way to get on his bad side: Relax. You are most assuredly already there.
Favorite person: Mom. Now, whether this means his biological mom, who he's never met, or the great Mother-God of the Silent Hill cult? Even he's not completely sure.
There's no guarantee he'll be 100% happy to see her should he ever accomplish his goal of finding her, either. There are years of abandonment issues simmering here, after all.
Favorite person met on the comm: In
dramadramaduck? Mio Amikura, most likely. Perhaps because she was nice to him, or perhaps because he has to respect that supernatural-repelling camera of hers. More likely it's because Sae Kurasawa's ghost has been visiting him since he started hanging around Mio.
Heather Mason is his second favorite, if only because he knows he annoys her. She's another Silent Hill resident, and so they're almost neighbors. Besides, he knows alllll about her dubious past. He thinks it's funny she doesn't want to be the Sacred Woman sect's big cheese. Doesn't she like all the attention?