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. 

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.).

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.

No, it is inside of an HOA neighborhood but the current regulations only restrict rentals under 30 days stays.

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

Landlord-tenant regulations are a bit complex in California and getting hands on is the best way to learn before expanding into larger investments. 

Proper underwriting - this includes an appraisal, loan app and full underwriting to comply with CFPB regulations.2.

However, there is no specific holding period contained in the tax code or regulations and there is no "safe harbor." 

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). 

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