If you are going to replace the roof and windows anyway, I’d go with a gray roof, black windows and sconces, and paint the house white (I think the vertical siding fits the house, even if you replace it).  

In my experience so far, I've only run across people with one or two options that don't actually fit my requirements anyway. 

We screened the tenants over the phone, via their online application, by interviewing their bosses and current/former landlords over the phone, looking at their social media, background check etc. without coming in physical contact at all.

If you were working with me, I would tell you the requirements I need, and you would just bring me the properties as they fit my criteria. 

You own the inside living space but the owner of the building owns the land and physical building, so maintains the grounds and externals of the building. 

Definitely will weight my strengths and weakness and what fits me best.

I had no idea of this and now I have to physically go pick up rent from her because she doesn't want to pay a fee, which i totally understand, I wouldn't want to either. 

I accept the risk, I take risks all the time,  both physical and financial.

. - If either set of us (both my parents/ both the wife & I) were to pass somewhere along the way, where do the children/heirs fit into this at all?

Redford, MI (B-,C, Neighborhoods)Warren, MI (C, Neighborhoods)Buy: $60k-$80kRent: $900-$1200Cash on Cash ROI: 12%-15% (Financed, Property Management, conservative savings)Cash Flow: $200-$350 a door (Financed, Property Management, conservative savings)Plenty more opportunities, more aggressive or more conservative, but these seem to fit your taste the best.