5k to learn this stuff?

Anytime the government tries to control prices, like they do with insurance in California, the market will react. 

He is month-to-month.

I have 2 other monthly loan payments I would like to pay off or lump in with my refinance as I believe with the forced appreciation and normal appreciation I will be able to pay off most my HELOC (5.99%) and all of my Credit Card that is currently at a 0% APR until end of May.

The automation is helpful to the emails that you send to the text, this is all nice to have along with great drip emails for birthdays, reminders in escrow, and much more. 

A two bedroom 1,300 sq ft cabin is going to go for way less than a 2 bed, 2,400 sq ft cabin.One of the issues out there too is that some are setup as legal 2 bedroom cabins because of the septic but then they have lofts and such that allow you to rent them out as 3 or even four bedroom cabins to improve the rent.You mentioned one nearby you with a similar layout.

Best way to learn an area is to drive/walk around as much as you can.

We are starting out with flipping because, as @Mohamed Youssef stated, we would like to build up a bit more capital.

Although, I am an advocate of documenting and creating systems, in the first few years all of your systems are going to change many times and so are everyone's roles within the company.

Are you looking to grow locally, out-of-state or no preference?