To me STR and hotel caters to different groups of travelers and so despite competition as long as the travel demand of Hawaii remains (as you pointed out is a robust assumption) I think both will continue to do well.  

In the long run, Roth-style retirement accounts beat the Traditional retirement accounts.

Take your time to clarify your goals, and be ready to continually learn and network along the way.Remember, each step you take is a valuable experience that brings you closer to success.

If you value the relationship and want to continue it, compromising with her would be in your best interest.

I've lifted the ban, you are free to continue to send messages.

One of the ladies, Amanda couldn't keep her eyes open during our meet and greet, she continued to nod off and she is one of their tenured Property Managers.

I would just continue to grind over the years until you have the ability to pay for the DP yourself. 

I'd recommend the following:1) Continue to stay at home to save up more2) Buy the crappiest home in a good neighborhood, with financial help (parents?)

I realize this comes with the STR business but if I'm going to continue to use VRBO I need to find away to attract the "good" guests and minimize the bad ones.

You learn a lot about real estate and get exposure to a lot quickly, most big firms will pay for you to get your RE license as well.best of luck with CONTINUING your real estate journey!