Do you have any books or resources out there that he can dive into to help him hopefully avoids some of the common pitfalls?

Eventually, I realized that if I kept waiting until tax time to organize my books, I would never escape the stress (and extra CPA fees).

Make sure you tune into the podcasts and read some of BP's books!

We already have a few mid-term booking requests so just as I thought, my vision of what's possible is coming to reality. 

As for the initial post, I would ask a few questions to shed some guiding light.

I just want to make sure I do everything by the book.

Instead of a pile of books or printouts at least you'll probably walk away with some money when the deal's over.  

Hospitality, attention to detail, cleaning/handyman team, programs used for bookings and calendar organization, inventory audits, home maintenance, etc. are all extremely important but all of that doesn't even begin to describe all of the things an experienced property manager does.It is a matter of how much time and energy you have to invest in your properties and if that time and energy is worth it to you.

I've read many of the BiggerPockets books like - House Hacking- Flipping- Estimating Rehabs- Multifamily Millionaire Book I and II- How to Invest in Real Estate with Low or No Money Down- Investing from a Distanceand even some outside of themand have been wanting to do something in Real Estate for awhile.

have strong desire to venture in real estate and have read books about real estate and the book I'm currently reading directed me to get more insights from here!