You failed to rent it in October before the holiday season. 

He is a seasoned investor and very well-versed in REI.

From the financing side of things - keep in mind that conventional cash out refinances require 12 months of seasoning in order to use the new appraised value.

I want to ask ya'll seasoned investors if you were starting out today where would you start investing with all the experience and knowledge you have now?

I would check this out with a seasoned securities attorney for their opinion/guidance.  

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

Meet-ups via local groups or via zoom calls or private REI clubs/groups.Asking a seasoned agent in each city/county as well as a Banker/Loan officer will also help put a plan together.

While it will likely give you more confidence and answer a lot of questions, I would say that talking to a seasoned investor, or even agent that works with investors, is a way better idea than spending 8K on something that you don't know too much about, especially before your first deal is done.

I'd say each property on average has at least 2 bookings a week ( more during the on season) so that's about 34 hours a week average.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.