Water might have been there for 2 years.Another house had a hole in the roof, not visible from the ground, possibly for 7 years.Another property the 100 year flood level is 8 ft above ground. 

The AO could have inherited the property, maybe a 2nd home, or a landlord.  

I do not want to send them the same type of letter as my AO letters but can not decide on how i should approach them in the letter.

But, on the flip side, you don't have a monthly mortgage, and can last much longer without a tenant financially.Personally, my comfort level is to have commercial loans on smaller (1000-1500sq ft) single family homes.  

What's her skill level?I

All utilities are metered separately with tenants paying.Specs of the property are as follows.Built in 1920. 2,200 total square feet(1100 per level) 3 beds/1 bath per level. I

There is no "good path", just depends on your mindset and comfort level. I

While I have a general idea of where that level is I cant confirm until I have more concrete financial data.

The guidance about finding a contractor who can list out what needs to be done at a high level is a good one.

The knowledge level is high and the networking is wonderful.