Not sure if that would be idea in Florida, but i certainty enjoy visits there. 

As a local we enjoy the tradewinds maybe once every year.

As mentioned everyone's strategy is different, I'm risk adverse & enjoy liquidity.

So enjoy it and be persistent, and patient.

If the answer to the last question is because they would rather stay at home and don't want to get a job or they have a job, but want to 'enjoy' their lifestyle and not be 'burdened' by bills, then it is time for them to grow up and move out.

So, I accepted modest appreciation (doesn't really look that modest since about 2020, honestly), and enjoyed a steady income. 

If I were you, I'd keep enjoying that income and manage it yourself - thus increasing it.

But like @Lucas Carl said, life might be way easier if you make your money here and enjoy a stress-free vacay in a prime destination.

One great way to scale a portfolio is gaining skills with plumbing and other repairs and taking the time to do the work yourself.If you enjoy working with your hands you can save a fortune by learning to do as much of the maintenance on your properties as you can.I get it that some folks would rather hire someone - I like to look at it as though I am getting paid the difference between what it cost me to do the work vs. hiring a tradesman.

But he said, "I never want to have another month like that because I didn't have time to enjoy my life".