Because this would be my first deal, I guess I feel like I should know what I'm doing before investing in markets that are a plane ride away. 

I currently don't know where you are in your investing journey, where you are trying to go, or if you are walking, riding a skateboard, or driving a Lamborghini.

It's only a short plane ride away and continues to appreciate in value, giving investors strong returns.  

Some suggested ride share or bus.

Come on man, maybe I wanna hitch a ride on the mothership too.....

If someone rigged the game before you even came on board you are along for the ride.  

LOL upside is the bills will get paid, downside is it could be an annoying ride for me :)!

Focus on Cash Flow Early On:While appreciation is the long-term play, as a beginner, I'd recommend focusing on cash-flowing properties to provide you with a safety net and help you ride out any market fluctuations.

Maybe STR has morphed from an investment into a business, and as such people who want to passively invest in it need to partner with full time business STR.  

Another may see it from the perspective that they've been getting a free ride all this time and now the party has ended.