If the insurance makes the numbers not work then yes walk, but if its more about the risk of being in a flood zone - 1/2 of florida is probably in a flood zone and its all about how comfortable someone is with the risk. 

How do they know if this is an owner stay that you blocked on your website, and it pushed over to Vrbo?

But you can't stay on title. 

I'd like to stay under 400k, am I too late to the party?

It really comes down to what you are comfortable with.

I just started working with THD, I had the same situation as Shankar RamaniI had a 3/2 SFH posted for LTR, they reached out asking if I am open to short term rental, I was hesitant first but after searching the company and their business model, I was willing to take the risk if they pay me a good premiumThe person who reached out to me works with the insurance side of THD ( they have corporate leasing department too), and her tenant had a fire damage in their house so the insurance company wanted the tenant to stay somewhere until the house repair is done.

As for leasing, I feel comfortable in that area market to get $14/sf.

It is big impact on short stays and less impact on longer stays. 

Or anything I should stay away from talking about? 

As an owner-occupant living in one unit in a multi-fam, you will have more leeway in who you can and can’t accept according to the law, but it’s always important to be aware of the rules to make sure you stay in compliance because you want to avoid having to defend yourself from an accusation.