We are relatively strict, but it has worked great.

That seems like a strict requirement of needing to keep the home for a year to use the owner builder direction, but I would confirm that before fully going forward as the GC. 

Rentals may be tricky considering the strict state laws. 

I've heard that the Sarasota County is in need of money (and that's the reason AirBNB deducts taxes and directly passes them to the County) - how strictly are those rules enforced? 

Is the tenant responsible for all interior and exterior pest problems or is it strictly interior?

Great input, @Greg Scott and thanks for linking those articles.I honestly hadn't even considered HELOC interest deductions, and it's not surprising that the IRS & banks have strict guidelines around this to protect themselves. 

It's also essential to understand local regulations regarding short-term rentals, as they can be strict.

Start up cost have strict rules too.

I go with strictly A+ rated vendors/companies and still check reviews online, but I've found that BBB reviews and ratings are a good indicator of how efficient they are.The 'manage the PM' seems to be a tough reality of the PM industry.

I am very strict when it comes to smoking.