I’d be looking at every flat surface of collection above, all the way to roof.  

On the surface, it seems like it meets a lot of broad criteria for being a positive investment, including a positive cash flow at a currently high interest rate, but I don't want to miss on my first step into this.

@Jacqueline Lee I'll 1 up what @Evan Polaski mentioned....Each jurisdiction and city is going to be slightly different, but at the surface there is generally slightly more paperwork to get your property approved and into the system, but once you get it up and running and the first tenant in there, its generally straight forward to get the rent increases etc.A good place to start would be your local housing authority, they may even offer "Landlord" classes to understand the system more.  

.)- Financial Services (you (owner) should think about what you want the PM to handle, if it is everything from paying bills to insurance procurement to P&L statements then ask that, if you don't want the PM so heavily involved in financials and just more on the surface level of the operations of the property then that is okay too!

If I can purchase this property smoothly and it all works out then I know he will be ready to start selling me his other properties in the same fashion so that his trust just receives a monthly cash flow payment from them instead of his family having to deal with the properties when he's gone. 

So, even if I had the exact same color, I would have three different cans of paint for each of those surfaces. 

While you can't stop the tenant from doing their own tests I would have not relied on that at all, especially that kind of test if I understand what that is, I mean, that is not a scraping or a sample from a surface. 

I redid the entire house (drywall, HVAC, roof, landscaping, kitchen, bathrooms, and surfaces).

Yes, as long as it relates to the renting of the property in some fashion.

Lenders are still unfortunately tend to be very conservative on the rent-by-room (SRO) type arrangements still - its an area that really could use some better understanding out there but just be careful with expectations because a lot of the treatment of these properties (even if nothing like a old-fashioned "boarding house") can be tough