However in my city a permit is required to list on Airbnb for 30 consecutive days or less.

Many of our first time investors utilize seller financing because it requires minimal downpayment for each investment property.

On the sell side, my local properties have performed great with no hurricane risk.Mother Nature can be unpredictable and impact RE performance, time required, etc. 

To maximize the number of transactions you’re involved in you will need to:Be Top of Mind when they think about moving - which requires consistent reminders.Be seen as an Expert – which requires a consistent message and Evidence of Success storiesGain their Trust – which requires communicating integritySo, start out by listing everyone you know in an Excel spreadsheet.

Which scenario leads to cheaper, after tax cost of funds, balanced against your risk tolerance?

@Kelvin HeSome things to consider:Transfer Taxes: Some jurisdictions impose transfer taxes when property ownership changes, even if it's to an LLC you own.Due-on-Sale Clause: Check your current mortgage agreement for a due-on-sale clause, which might require you to pay off the mortgage if the property is transferred to an LLC.

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

To maximize the number of transactions you’re involved in you will need to:Be Top of Mind when they think about moving - which requires consistent reminders.Be seen as an Expert – which requires a consistent message and Evidence of Success storiesGain their Trust – which requires communicating integritySo, start out by listing everyone you know in an Excel spreadsheet.

If the tenancy is at-will, you can deliver written notice of the rent increase by giving the number of days' notice required by F.S. 83.57. 

While it is not required, it seems like an easy gesture of goodwill.