Within the next year or two I hope to get more involved and ideally purchase a duplex to rent with the possibility of "house-hacking."

Watch the movie "Boiler Room",  (I know they are pushing penny stocks, not blue chips)I always say when raising private money investors for rehabs...."

I am nervous about jumping in head first to situations I am not familiar with so that why ideally I would like to do a couple deals with some one or even sit in with deals they have going on to earn what the basic process is.Like I said any help from fellow BP would be amazing.

I know richmond and east oakland aren't the "ideal" places to live in the bay area.

I want to engage in the full gamut of activities, including wholesaling, sub to's, fix and flips, and ideally fix and holds (for at least a year).    

Include closing costs.3: Ideal Month Income.  

Hoping caseworkers come out to visit or whatever when i'm around to appoach this for what it really is.. but how should i deal with this?

@John White yes this is ideally what I'd like to do - even open to a single family with an inlaw for me to live in.

That may not work in every house or neighborhood but for our purposes it was the ideal situation. 

I deal in some neighborhoods like you're talking about - lots of property crime, low violent crime, Section 8 rentals, lots of lazy people, etc.