What will it cost to buy a property vs. what will it cost to rent?

We were also looking at a TON of houses in the area so we knew this house was under what it should have costed.

At times, I wish I hadn't even touched certain things as it cost me more to hire out a contractor to fix my mistakes, and other times I have saved myself a few hundred dollars on maintenance costs.

What portion of the deal did those managing funds get wrong? 

He knows the areas that you can legally air bnb, what specifically the property is going to need to maximize bookings/ROI, and has the property management contacts to optimize the ROI. 

I have a background with owning rental properties, managing STR, MTR, and LTR tenants, and flipping all in the area.

If so, you could look more for turnkey properties and focus on learning to manage them effectively.

Curious to know cost of mentorship, 

And yes, he should be giving you his crew, the subs and materials at his cost.

Are their flipper secrets to getting materials at a lower cost?