Quote from @James Hamling:Principles for Dealing with the Changing World Order: Why Nations Succeed and Fail, Ray DalioLegendary investor examines history’s most turbulent economic and political periods to reveal why the times ahead will likely be radically different from those we’ve experienced in our lifetimes.AWESOME picks....start with Dalio. 

My parents had a couple of rentals and I know people who have been landlords for 30 yrs.life styles is a good place to start if you have no knowledge, they will give you the tools necessary to succeed. 

I could look at nearby properties and their tax value on the County website Any advice on which of these 3 options is more likely to succeed? 

If you're willing to put in the work and make the sacrifice you're going to succeed. 

Also, you MUST know the pros & cons so you succeed and don't lose a significant portion of your investment.

@Pat Quaranto you may consider narrowing your focus down to become an expert and increase your chances of success.Do you think it's easier to succeed at something you're an expert at or wherever the winds blow?

Just my two cents, not to say you cannot succeed the other way around too!

Rather than second-guessing "what is the new hot STR market" as I see many do - I may be biased - I believe it makes more sense to invest the time in figuring out how to succeed in a year-round market which is proven to attract tourists year after year.

However, do you think that the program ultimately exists to assure that you succeed or does it exist to make PM money?

@Gabe Knowles pretty much what @Travis Biziorek said.One of the best ways to succeed in this business is by hiring experts and learning from them so you can do it yourself the right way going forward.Trying to do it yourself and learn as you go, will usually cost you WAY MORE!