@Kevin SiYes appreciation is not guaranteed and it clear your realtor has less than 10 years experienceWhat if you have 0 appreciation and your taxes and insurance double over next 3 years?

This would be DSCR based product (no tax returns or DTI needed) but keep in mind business purpose loans in Florida can only be made to an entity (LLC or Corp). 

Your rentals should only perform better over time as rental income increases faster than property taxes, insurance and other expenses.How much will that contribute to your retirement income?

We are not tied to a particular coastal market, since we understand that certain areas have higher taxes/fees/regulations/hostility to STR/flood insurance/etc. 

Lenders generally require you to have at least 3 months of reserves or cash that will pay for mortgage, property taxes, insurance and HOA (if applicable).Most lenders will generally lend on 1-4 units and condos.

I have cross reference the mailing addresses with the county tax records on thousands of records and I would say they are 90% correct and the sale dates are within two weeks of the actual recorders office dates on title record. 

Didn't I just see a proposal that would change STR classification so that they will have to pay 4x in property tax?

I'm a property tax professional (reducing taxes for commercial property owners) living in Northern Kentucky.

Stocks are pretty liquid, BUT selling them triggers tax consequences and the timing of when you want the money for real estate purposes might not coincide with the best time to sell the stock.

Hire a tax professional to help set everything up.