Most hard money lenders will want to know about your track record - if you have no experience, partnering with someone who has a track record will likely be an easier path to approval (and likely higher leverage) than applying by yourself. 

So curious if that still applies or if it's bank by bank. 

I know this doesn't crack the 1% rule but because we are putting more than the minimum down we still cashflow.  

What you stated only applies to St Pete itself, and not unincorporated Pinellas county.

Apply here: https://airtable.com/appnZ2AGUknfciOzu/pagvbFaEPNprDBVKi/for...

My only concern is searching for the rent to value "1% rule". 

If the trust holds the insurance, it shouldn't matter.That's correct but changing the beneficiary to someone or something other than the borrower does trigger the due on sale... no exemption applies. 

There are rules to follow!

Since you’re considering converting the upper unit into a short-term rental, you may also want to implement strict rules around smoking or strong odors in your house rules to avoid future issues.

Both Fort Lauderdale and Pompano have fairly relaxed STR rules and regulations.