First rental property - vacation rental?

[David Goldenberg]

A bit about me:

I currently live in possibly the most expensive area on the planet. It is cheaper for me to keep renting instead of buying here, so I do not own my own residence. I have a high salary day job which I enjoy very much. I am more interested in generating wealth and maximizing tax incentives than cash flow because I love my day job. 

What I am looking for:

I would like to invest in real estate as hands-off as possible with professional property management. I need to look outside of my general area because there is no way to make the numbers work here. Because I would have to do long distance investing in general, I am considering purchasing a vacation rental. If the property is going to be far away, it might as well be in a place that I would actually want to go visit! This would be my first property. 

Anyone get started with vacation rentals before buying their own house?