As I see it in the current market, STR is now a way to get a really good, appreciating asset to pay for itself, not a way to produce a meaningful amount of cash flow after all expenses. 

Craigslist wasn't pretty, but it was easy to use, and it worked (I found lots of great tenants via Craigslist) ...unfortunately, over the years, Craigslist produced fewer and fewer tenants, and more and more spam.  :( These days, nearly all my new tenants come from Facebook Marketplace.  

I was the oldest boy so naturally I helped dad with all the renovations.

Naturally, she wants to be in a more comfortable environment to welcome our son into the world.However, there’s a legal hurdle.

Start with whatever your son's natural talents and inclinations lean toward.

Other distractions include non income-producing activities - aka any distraction pulling you to do something other than speaking with and following up with people.How can I prepare myself?

I would also recommend looking at cities close to Greenville, like Anderson, Easley, & Simpsonville as well since Greenville can be competitive unless you are looking at off-market deals.Also the non-occupancy tax would be based on the tax assessed value of the property and not the income it produces.

And natural wood interior walls for that cabin feel.. can you post a link to what you recommend a  cabin should look like I am just curious . 

Naturally my DTI is high, however my only debt is our primary residence mortgage I have had since 2020.

Due to the nature of the STR property criteria in Cape Coral, it's very rare that a STR could be converted to a successful LTR.