The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

There are opportunities out there but some strategies are risky. 1 - Airbnb (STR) comes to mind - very competitive, very saturated and becoming highly regulated.2 - Most STRs are transitioning to MTR so that market will be saturated soon if it isn't already.3 - Insurance crisis in florida is getting bad so those costs will eat up cashflow and short term appreciation.

True although the fires this year just adds to the reasons to leave California (excessive taxation and regulation, overbearing political correctness, downtowns littered with feces, etc.).

I believe Hawaii will continue regulating STR and it will be harder to make the numbers work. 

As for Alexandria specifically in terms of regulations don't take advice from a public forum - look up the laws yourself and make sure you understand them.

Another huge thing to consider is laws and regulations, many times new investors will jump at Hudson county thinking the proximity to NYC is great for renting (which it is) but many of the municipalities in Hudson county have very strict landlord laws. 

One of the other factors that kept me from pulling the trigger is that the city has never passed any real STR regulation.

Ensure that you thoroughly review your state regulations and display the necessary notices before changing any locks or removing any items left behind.

To get started - I’d recommend connecting with local STR investors and researching Hawaii’s regulations.

He also doesn't control regulations in the states/cities, but his attempts to cut regulations may trickle down and impact personal property rights and people's ability to use their properties as they see fit.