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

These are the primary factors that will guide your choice of market and the type of deals you'll pursue out of state.Investing out of state can be tricky.

Quote from @Niranjan Sathish: Hello, I am Sathishkumar, have been learning about Real Estate through books and podcasts for the past couple of years. 

It sounds like you may be a better fit for a smaller operation that still offers guided tours.

I've read BiggerPockets' Real Estate Investing book and am particularly interested in the house hacking strategy, as I'd like to move out of my current living situation.Our main dilemma is choosing between a single-family home (renting out one room to a close friend) or a multifamily property like a duplex or triplex.

I was just reading Mark's book "The Tax & Legal Playbook" this morning and it specifically had a "critical warning" (page 31&32 in Chapter 3).

We don't have any issue getting it booked up for the season.

Here's a detailed guide on how to screen applicants: Application Screening Guide

As you look deeper into Cleveland, check out The Ultimate Guide to Grading Cleveland Neighborhoods.

Everything you learn from books, podcasts, seminars, and websites is general information.