We’ve talked to other investors in the area and one advised us to avoid Pinellas county if the property will need any significant work due to their building department.

I'm curious what advise other long term hold investors, specifically with more experience than us, have about transitioning from live-in homeowner to landlord? 

I need your advise.

Thats the best piece of advise I can give you. 

There are a number of reasons why you might do this but it’s usually based on achieving better terms (rate, amortization, higher proceeds, or non monetary terms).

Other's are necessary to maintain the value of the house, like the gardener.But I have been advised to pay all the bills in order to keep her name from being on anything so that if it ends up in court, my case for evicting her will be easier to win.

Please advise. 

That's what I would advise.

@Kevin Stringari I have listened to interviews with one of the owners of those security deposit insurance companies and most of the time they will not pay out a claim unless you have a monetary judgement.

Readers are advised to seek professional advice.