Far too many get stuck in the "paralysis by analysis" stage, thinking they just don't know enough to get started.

This is privately arranged property management. 

Then figure out what software they're using, find out what insurance & licensing you'd need, how much in-house our outsourced staff costs, and try to come up with some figures for revenue and expenses at different stages.

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.

I am not yet, I was in the stage of educating myself and have been networking at my local REI, but obviously they mostly work in Raleigh.

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

What is needed is staged protection combining multiple layers, and its not very expensive.

This is a great place to start and learn about real estate regardless of what stage you are in!

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.