There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

I plan to sell and 1031 exchange this property in the next 12-18 months.

If you don't live in Washington then join all the "Washington/Seattle Real Estate Investor Groups" on Facebook and ask this question in each one.

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'm in the early stages of considering a venture into the short-term rental business in Austin.

Purchase price: $225,000 Cash invested: $50,000 Fit criteria of A and B rated school in good area that could appreciate over time.

For further learning, here are some solid bookkeeping books that can enhance your knowledge:"The Book on Managing Rental Properties" by Brandon Turner – This book covers not just the property management aspect but also has sections on bookkeeping and managing finances."

They go over a lot of the fundamentals that I completely agree on as a high skill operator in this space.  

If you have any due- plexes, try-plexes, four-plexes or mother in-laws, please reach out to me.

You don't really mention investing in real estate, so this is just a purchase for your personal use.