Of course Kissimmee is a year-round market, and becoming even more so as families have the option of traveling year-round due to working remotely and virtual school in many cases. 

I travel through Dubai periodically for work, and I feel like I can't afford anything in that city.

I used to be in it all the time but with how much I am traveling it's just not worth it.

I plan to traveling there very soon to meet my core people needed to make this happen!

Domestic air travel has been slowly increasing at L.A.

Another thing to think about is picking areas you either travel to alot or would like to travel to a lot.

One thing you have to keep in mind is telecommuting is happening alot now but once travel is on again many companies will want to see employees "live" at least some of the time and companies don't like to pay large travel costs.

Your Realtor is correct, the further out you travel the less effective a rent by the room model for house hacking becomes.  

TBH, I probably wouldn't even travel a few hours away until it was under contract with an inspection clause so I could get out of the deal if things look ugly when I go see the house with my inspector. 

Lots to learn, and lots of different ways to travel.