Also @Tim Phillips something to be aware of in FL, all condos older than 30 years and taller than 3 stories are required to have a "Structural Integrity Reserve Study" performed before the end of this year.

First, have a conversation with an accounting firm to see if a cost segregation study will be beneficial to you.You don't want to spend money on something where you won't get a benefit from.

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 realize that a full feasibility study will most likely be required if I move forward with an LOI and purchase contract.

I guide clients who are looking to treat their STR as active.Somethings to consider are whether you should get a cost segregation study done, creating a log of your hours and having an understanding of what hours count / don't count.

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

@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