stucco layer seems very thin.

I don't know of them, but from the looks of the website you shared, I would say they are fairly inexperienced in a few areas that are vital for you as a passive investor.  

Leave a small boarder around the house, put down a thick landscaping fabric and thick layer of gravel. 

You can then control that IRA owned LLC and use the LLC as your transacting layer.

                                                                                   -4 to 10 layers of roof since the early 1900 (never replaced just covered up)                                                                                                  -No insulation between ceiling and baseboards, no insulation under roof material, some tar and some shingles                                                            -My current problem for the last several months is rain/water coming inside the unit.

You owe it to yourself to slow down and evaluate what's really important and vital in your life and then transpose that to others.

After we got in and were able to see the roof, it looks like it's about 15 years old and has a couple layers of shingles installed.

@Mya Toohey thank you for your answer, I think that a mentor will play a vital role in my real estate career, But that begs the question, how do I find one?!

So it is wise to be wary of these.The first line of defense is having the correct commercial insurance policy.If you have a mortgage with a good chunk of debt that is another layer.The VRBO and Airbnb insurance would be another layer if it holds up.I have seen no need for me to get an umbrella policy.

Maybe landlords will finally listen to what I am saying.This is not the solution for you.https://www.washingtontimes.co...This is .....Dear President/Govenor/Senator/Congressman/HUD Secretary/Govenor (You Fill in the blank)Thank you for all that you are doing to help citizens and businesses affected by COVID-19.As you are aware, Landlords provide a vital service to many millions of Americans.