¤ hobo santa - santa symbol on map, north of café, east of diner. I can't remember how it unlocks, but he shows up randomly at school during the "socialize, meet new people" activity I think. you bust him peeping.
¤ heist for the redheads - get caught by cops in your car until the redhead shows up, then do it again next day until she tells you about her problem. this should unlock the heist option.
¤ I can't set the fire in the hallway trash. - maybe you know someone in school who's known for setting fires?
¤ convince her i'm not gay - in school do the bully/tomboy things, then skip class, get detention, go to the gym, fight the bully, talk to tomboy, follow her (need 25 sneaking) have sex with the tomboy, almost get caught by the bully, bully beats you, sister finds you naked with bully and thinks you're gay.