And it had some updates done before selling.Because I am new to investing and kind of risk-averse, I am more leaning towards buying in a safer neighborhood and learn how to manage/maintain a rental before buying fixer-uppers that can create higher returns.My feeling is the asking price is too high, if I can negotiate and get it down to $370,000, it would be a workable.

(That would be a workable deal)I don't specialize in the east side but I'm a full-time landlord/investor who just happens to be Property Manager (in my area and for select owner personalities...we don't skimp on the tenant strictness or holding our owners to owning safe, well-maintained houses.) and I am a realtor in my free time. 

Following advices from the pros on BP has put me out of my comfort zone but I can say that they have worked and i was able to build a workable buyer's list within 3 days.

That is, assuming both parties are clear on what they agree on and there is a minimum of trust or workability?

So this might be workable if you're going to buy a multi-family and live in part of it, but not for a general investment property.

Probably could use a good cleaning, but may be livable otherwise.I suppose if the owner gets desperate enough an owner carry may be workable.  

I've read here and heard elsewhere that with seller financing, the TERMS are where it's at and not necessarily price so I don't want to "price myself out" of this with the traditional wholesale formula if truly there is money to be made with a different, yet financially workable approach for all involved.What questions should I ask and what should I be listening for?  

Is this workable?

Possibly roof, HVAC and a new driveway, if "required".I would like to know what balance other investors have found "workable".

Each unit is a 2/1, the bedrooms are fairly some, but I believe they are work able especially with then location.