Get rid of him immediately.One of the most important skills to learn as a landlord?

This is what I heard third hand, so not sure if it is true but i believe the person got this from the PPM which was noting where the monies were going. 

I'm not saying one shouldn't seek advice and learn up before taking a giant leap for mankind, however the importance of ACTION, itself, I can't stress enough – especially in today's world of information overload.

(Either with the roofing company, a heloc, or a personal loan.)Either way you will probably be way ahead on interest saved unless you have a sub 6% interest rate.

I'm willing to help this person in any way I can.

Right now, I'm focused on:- Learning the best investment strategies that don’t require a real estate license (wholesaling, rental properties, etc.).- Finding potential clients who are interested in investing but may need help identifying great deals.

You've started and will be able to learn by doing.

Once again, this matches my personal experience that the larger, more expensive properties continue to sell better than smaller properties. 

Lessons learned?

Quote from @Dereck Olson: Hi Nicholas,  Just a thought from the possible tenant's perspective, but filling out a prequalification form and/or providing personal information before they have even seen a place and know if they will be interested in living in the property might be a bit too much to ask.