Every single step of the process was mismanaged and it all felt very amature.

You've already taken the first step toward becoming an investor.

What is the best way/approach to go about this step in the process? 

I’m just kind of overwhelmed with the process since my very first step to take action is unknown.

I am in a similar situation (although I've changed my goals slightly and I make significantly less than you do).Your strategy is likely going to evolve as you grow into it, so the first step is about getting your feet wet.You aren't investing as much as you are building a business. 

You don't need to add the extra step of doing a cashout refi as you aren't keeping it and it costs a lot of money to cashout refinance.

My thought is is use the Rent Ready feature of reporting his payment history to the credit bureau so it can work in his favor as a trade line, but I'm wondering if this is an unnecessary added step since he can already pull transactions on his bank side. 

I ended up going with a market I had already been to, Huntsville, and learned to do long distance real estate investing as well as the BRRRR method.

I know very little about legal precedent but I'd expect the major meter manufactures (selling into the utility space) to be well incentived to challenge these items best they can, and they have money.Here are the issues, and the reasons that the difference between an air forced system and a boiler/hydronic system are not meaningful for this discussion (ie efficacy issues of sub metering exist for either when method of measurement is measuring heat at point of delivery):In either case, the blower (or pump for a boiler) is the method of 'moving' either air (central air) or water/glycol or equivalent (boiler etc). 

That’s a huge step, and it’s awesome that you’re looking to dive into both rental properties and flipping.One of the best things about being a member here is the ability to network with people at all different stages of their real estate careers.