It usually doesn't work out well...we  have purchased properties before to use as non-vrbo rentals that have been furnished (even with new furnishings) and it never fails that the tenant will ask to have "some of the furniture stay" and other be moved out. 

I would use your access to the MLS and deep search past Multi Unit sales back 20 to 30 years and approach them to see if you can work out owner financing to purchase if they are ready to sell.

He gives the strong impression that he wants to teach someone what he knows, and says he'll see if anything in this deal could work out for me.I'm an engineer, so I'm prone to analysis paralysis.

This is going to sound harsh but your expectations are way off track.

How can the IRS rely on a random opening balance on a basis schedule that does not track back to the prior year? 

Once this current pandemic is over I can get back on track of converting a 640sq ft detached garage into an apartment in Anaheim.  

At the time it wasn't easy to find banks looking for young investors with little track record.

You might have a property near a highway, train tracks, highly trafficked roads, but due to other buildings nearby or landscape, double panned windows, you might not even notice it.

(Alternatively, bill in advance for $X,XXX dollars to be spent on materials, and then provide receipt tracking for materials bought against that bill, billing additional as needed)The problem I've seen over and over again is that investors will turn contractors into unwilling lenders with none of the protection (Deeds) or benefits (Interest) afforded to a real lender.

I've been doing by due diligence, reviewing the economic base, tracking property values, following employment trends, checking off the boxes you know.