I would highly recommend proactive tax planning if you are in this situation.

Every step of the way it is complicated, counter intuitive, and time consuming. 

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. 

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.

Literally going to copy this entire post print it out and follow step by step! 

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. 

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

The process is pretty simple, but it does involve extra steps compared to a traditional rental.

What should my next step be?

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.