So, he hired a lawyer, bought some more land and started planting flowers in the toilets all over town. 

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.

If it is then spend the time getting the RIGHT education, building capital reserves, making contacts, and arranging financing options.  

Fortunately, I escaped any legal trouble because I worked out arrangements with the original sellers and gave them their houses back.

You're not going to arrange a typical "public auction", a bit delusional. 

A standard rental policy will not cover short term activity and make sure the insurance company is ok with the sublet/arbitrage arrangement.

The tenants will be responsible for arranging and paying all utility services required on the premises.” not very detailed I know I wish I would’ve done better but that’s what it says