Hi Stephen, I would suggest reading as much as you can and connecting with people in the industry.

You might find it useful to attend a meetup or two just to learn how other folks got their start into the industry :) I host a small/intimate meetup once a month in LIC, check it out here: https://www.biggerpockets.com/forums/521/topics/1214850-meet...

Buy on market, nothing wrong with that.

I am near the Nashville area so I am on the same boat upon learning more about the real estate industry, welcome!

I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

Have you considered which markets or property types you're interested in? 

Time in the market beats timing the market!

@Andy Ptak when jumping into the industry you have a few choices:1) Start at the bottom2) Leverage your experience to convince someone to give you a chance3) Decide between:--- Big companies who will usually start you at the bottom--- Small companies that will more like to a chance on hiring you for an above entry level position.

Depends on your market and competition.  

No market can promise you this.