@Kinni One last question, does the info we got on them tell us stuff about the actual occupants? Like, if one of the guys in the 8 person house is a high-school-aged boy?
Also, a question for everyone else, does anyone know how easy/hard it is to get animal tranquilizers/sedatives?
[X] Plan All But One
[X] You are going to rob all but the Richest House
-[X] The Middle class one is simple enough. Wait till no-one is there, pick the lock, and grab something valuable, and preferably small.
--[X]Back-up plan if someone arrives while you are looking for stuff, punch their face. When breaking in, make sure to act like you belong. Don't want nosy neighbors calling the cops, punching their faces will cause more trouble.
-[X] The Less Well Off House, pretend to be one of the (girl)friends of one of the male occupants, disguising yourself to look an appropriate age if there aren't any teenagers, preferably one that isn't there currently. Once you gain access, perhaps to that guys room while waiting for him to arrive from wherever, try to find and nab something small and valuable. It's easier to walk out with a diamond necklace in your pocket than a TV in your arms. Once your treasure is secured, make up some excuse to leave.
--[X] If the person you are pretending to be the friend of is there, try to get alone with them with some implied fun times, and then choke them out or otherwise quietly render them unconcious. Continue plan.
-[X] The Well-Off House, get some meat and some tranquilizers. Feed the dogs, wait a few hours (perhaps do one of the other heists during), come back when the dogs are asleep, and go steal something.
-[X] The Second Richest House. Gain access by pretending to be there sent by one of the bosses. See if you can bluff your way into taking something. If you can't, punch everyone's face.
-[X] During all these, make sure you are disguised to look like not-you. That way any descriptions of you are pointless, and preferably varying from crime to crime.
Here's some basic research stuff. I can't think of anything, in particular, we'd need to know for any of the houses beyond who lives there.
[X] Plant cameras watching the houses, set up mostly to watch the comings and goings. Knowing who will be there when will make your job a lot easier, especially for the houses you have a chance of slipping in when no-one is there.
[X] Focus on raising the level of a specific skill (Disguise)
[X] Learn a useful miscellaneous skill.
-[X] Lock Picking
[X] Use Hypnotic Trigger on Disguise
Disguise is far more useful than Lock Picking