While I understand appreciation isn’t something I should necessarily bank on, but I am looking to hold for the long term and eventually relocate to the FL.

However I am struggling to understand and evaluate the risks involved with cash out refinancing 2-5 years down the line.

If that is so, it behooves you to understand how much that fee is and when it becomes due.

From what i understand, the space heaters are a big fire hazzard. does your insurance allow them?

I understand if a contractor doesn't want to agree to it.

So, scope out the competition on #1 & #2 above to understand what the rental or sale market expects.- You will lose money if you go overboard!

You don't need to know everything to get started; you need a foundation to build on, and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

A good way to get an understanding of how to get into STR is :STRATEGY: Start Up Guide to Short Term Rental Investing 

It's crucial to keep investors informed about these factors and help them understand the rationale behind our long-term strategies.

I understand the condition of the property may not be great, but if you're just trying to get rid of the property, then why does the condition matter to you?