It is a mess and you are partly to blame because you are ignoring all these red flags.Write her a notice that says the home is uninhabitable due to the water leaks and you are terminating her rental agreement, period.

They don't have the red tape and seasoning conventional loans require.

I don't know about commercial loans, but some hard money lenders offer products that allow a flipper to refinance  or do a cash out without all the red tape and seasoning.

Is there any red flag?

go easy on me, I'm color blind and a terrible artist...heres what I put together...Rough sketch with the walls i want to remove in red, existing/walls I'm keeping in yellowhttps://drive.google.com/file/d/1h9Zsm8YeuIYLlbInY...Rough sketch overlay to aerial photo to show hip roof. https://drive.google.com/file/d/1OK90I7ikqJp6_7b7a...Attic shot looking west from the corner. 

Worst case is all hose red flags are significant and something is amiss.

I would see that as a big fat red flag

Like many other PMs, Matt Maurice from REIS does not manage in Trulia RED and ORANGE areas. 

If there aren't any major red-flags then I'll proceed to make an offer so I can get more time and really inspect. 

I've talked to the current PM, and while he's usually leery about managing non-conforming properties, he said the fact that the postal service didn't raise a red flag and is delivering to all four units is good enough for him that there'll be no issues with the county.