What are some best practices when working through due diligence at the phase of projecting cost?  

Living at home is great for saving; if you move out, make sure you get a place where you are allowed to rent a room to a room-mate so that you can continue to save money and also get some practical experience as a "landlord"

There’s probably asset protection specialists/firms  who will side with your approach but it’s not practical and they are just  fee collectors. 

Since you're focusing on Worcester, try pulling up some local property listings and practice running the numbers on them.

But does anyone have real feedback about how good the insulation is or how practical these homes really are? 

Conversion rate is extremely low when you get started BUT it will give you good practice speaking with sellers who have a ton of objections.

Any thoughts on best practices for converting equity in property into cashflow.

Quote from @Benjamin Weinhart: Hey Ben, I reference my old boss because I have never seen this practiced myself.

Any tips, tricks, or best practices you wish you knew when starting out?

None of the above works unless you take action and put it into practice.