Long story short I never got a chance to actually flip a house but a property owner offered me a gig screening tenants for his vacancies.

My first deal is owner occupied to is allowed me to put much less down up front.

Even if you are inexperienced, self-managing allows a lot  more control and you the owner has the highest self interest to get the best tenants.  

I actually work with an Insurance broker that I know the owner personally, so i've ran several scenarios by him on this and he says there are no issues whatsoever.  

We don't have these in MD but maybe you can have different owners of the different LLCs in the series.You say you have "passive" investors.

Spring may generally be the best time, but remember nobody can forsee the future.Or build a 2fam yourself and flip it to an owner-occupant come spring :)

I did go driving for dollars and found 2 properties that I am going to send letters to the owners so it wasn't a complete waste of time.

When selling a property via owner financing are there any terms beyond the obvious (price, term, interest rate, late charges, ect... ) that I should have my attorney build in to the contract?

The bank is concerned that they might do something wrong in the foreclosure process and want to protect themselves by shifting these problems to the next owner via quit claim deed. 

I look up the old addresses they sold and contact the owners for a real review via Facebook or LinkedIn.So far I haven't been able to independently identify a happy turnkey customer.