Some will succeed at having a roof over their head.

"Just a little damage" Walks flat, needs roof and cosmetics. 

It looks like one room is the dining room and the other may be a bedroom.If one of those rooms is a bedroom, you very likely have a roof leak.

The lots are almost all steep.

Most LLCs are set up for liability protection or similar non-tax reasons, and especially in CA, the penalties for "non authorized" practice of law are steep that a lot of CPAs will not even form the LLC for their clients. 

I also liked the fact that it was structurally sound with concrete block construction, a tile roof, and high elevation.

For the first part of your question even if you were working with a realtor, I don't personally know many that have a true pulse on rehab costs and I wouldn't make any investment decisions based on their rehab cost projections.My suggestion would be to study how to evaluate the Big 6 rehab costs: roof, siding, windows, HVAC, electrical, and plumbing. 

Year 2 had some large expenses, including some CapEx items (water heater, roof).

Some HIs will walk the property with you for a steep discount and tell you what they see to inform your offer.

We are currently looking at a HUD home in Georgia - I have a couple of questions and can’t seem to find a definitive answer - The home is currently in the OO listing period - our plan would be to buy the home doing extensive renovations (the home is in a “Historical” area so renovations have to be approved) once completed we plan on living there full time - it could take ip to a year to complete or longer I don’t know  - as I see it the OO designation is to be the OO for a min of 12 months - is this after the home has been renovated or after you close on the home - though the house could probably technically be lived in now it does have some water and roof damage and needs complete redo of electrical and plumbing - for me to deem it safe - so not really livable by normal standards - but no way it would be livable in just a couple of months - any thoughts or an actual answer to the OO rules