I know every tenant has to have a first rental at some point, but good people 99% of the time have good family willing to help them out to get that start.My point was more-so that if the PM and landlord agree on qualifications (which should be driven by the experience of the PM and their market knowledge), then the landlord is in no position to blame the PM if the tenant goes sour - we can't control the tenant's life, only mitigate the risk/damages.

That way I'll be more knowledge and maybe get a better deal in a year or two.

Don't leave it open to, "we will catch up when we have extra money".

If you uncover that answer, it may shed some light on the investment (maybe it's good info and it satisfies my skeptical approach)I have found the biggest three seller motivations (with landlords) are:1) Tenants are subpar and current owner is tired of managing (in this, you're inheriting headaches, eviction, and much higher repair costs than you expect). 2)  An estate took over and just wants to get it gone (in which case there is probably a back balance owed that needs to be flushed out along with a general lack of property knowledge). 3)  My personal favorite: the Owner bought via tax sale deed (and therefore does not want to be a landlord, just wants his investment + reasonable return).If everything checks out, it sounds like a great deal bud.  

You want an agent who is knowledgeable and who has multiple markets.  

As far as building and extra unit in the back.

My two large losses this year happened because of bad, fluffed CMA's that we went by because we bought before we had access to comps ourselves and had a general knowledge of the neighborhoods. 

Real estate has always been on my mind but I haven't really dove in to gain the knowledge of where to start. 

.- My goal is to follow Scott Trench's ideas in Set for Life and hopefully rent a room for under $1200/month to save some extra cash and use it along with my current savings to buy and house hack a duplex/triplex/fourplex in 4-12 months in the Oakland/Emeryville area.- I consider myself very handy since I have renovated my entire house 99% by myself and pulled permits. 

Getting my glossary together and my knowledge as sharp as I can before jumping in.