Note that my experience is limited to NC, SC, VA jurisdictions, so keep that in mind when reading this or my other posts about solar. 

We have bought three deals this year, and closing on a fourth next week.I'm also a life coach, and limiting beliefs have held me back.

Plus, in FL, property managers are very limited in what kind of an eviction they can file.

The period during which it was rented as an STR may allow for partial deductions, but transitioning it to personal use would limit the amount of depreciation you can claim going forward.

We can definitely explore options for a mortgage on your $350k property to fund both your current renovation and the purchase of your next investment property.For the new property, we can also consider a separate mortgage to cover its purchase and rehab costs.Regarding the rural location, while it may limit leverage to around 65% of the property's price/value, we can work within these parameters.Given your equity position and experience, I'm confident we can structure a solution that meets your needs.

I don’t actually know about such situations, as I’d think it useless to file a Stay of the Writ of Possession at that time… This is way above my limited knowledge.

They do this to limit risk.However, some lenders may be more flexible if the deal is particularly strong, and your experience or financials are solid.

So STR loophole there are personal use limitations: To avoid having the property classified as a "residence," which limits your ability to claim rental expenses, your personal use of the property must not exceed the greater of:14 days per year, or 10% of the total days the property is rented at fair market value

Location, location, location is the key.I am not as convinced that a limited season is a huge drawback.

@Marc ShinI'd hire professional management...If it's going to be an STR, you really need it to be top notch, appear top notch, and be managed top notch"Minor updates" may not cut itBut I only have the limited information you posted