His COO was supposed to call me yesterday with a pre-arranged time and he never called.

But each year the IRS has continued to shoe their dislike and distrust of the arrangement. 

You will need to learn about the local laws, advertise, background check applicants, meet them for showings, answer questions, get a good lease, answer the phone at any time, arrange for repairs, do inspections, manage finances, manage an LLC, and more.

Are there any verbal agreements or arrangements between the current Landlord and Tenant?

Of course, he could become a broker to make and arrange loans among others.

Does anyone have experience or advice on this type of arrangement?

This is privately arranged property management. 

I will continue to look at Springfield and am also exploring Longmeadow and East Longmeadow as I hear that location may be better suited for mid-term rental or rent-by-the-room (CoLiving) arrangements.

Ummm... as others have noted, nothing is "free" and yes they are probably including the price of a "cheap" new roof in their arrangements. 

I've watched a ton of BP podcasts and videos but I'm brand new to the forum.My long story short is that my wife and I had our second baby on the way and although our rent arrangement is very favorable, we needed to upgrade for more space.