Also, if you are a minority, WRA has the Partnership for Success program, which helps pay for your start up costs.

They don't provide the data first.

A prudent investor doesn't seek quick riches through shortcuts.

There are a lot of things that can come up on a flip so easing your way into things and working your way up to larger rehab budgets, etc is recommend.

I’m brainstorming ideas on how I can market myself to potential mentors in the STR game in order to gain experience.

Here's a good breakdown of your options for tax collecting starting Feb 1 based on the new regulations.

The most reliable way is look at other STR's in the area and see what their nightly rates look like over the year and look at their occupancy rates. 

I found houses that had not been well kept up.

Is the backup to use it as an STR during these months?

@Marc Zak Using an LLC for each property provides strong liability protection by isolating risks to individual assets, with income and expenses flowing through to your personal taxes on Schedule E.