The fact I can go to my kid's golf game today, yet still catch a vendor overcharging me $81 the day before on a SFR in Georgia makes me feel the systems that are in place, plus the ability to manage sacrifices has paid off.I've had the same team in most of businesses for almost 8 years, and have a growing RE team that continue to impress me. 

Right now its slim pickings in real estate for properties that will cash flow or see any significant appreciation. of course they are always out there but a lot harder to find.The other question is why do you want to continue to grow?

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.  

Personally, if your market tends toward the former condition (better/normal appreciation) I think it's a fairly safe deal looking at the long term, assuming infrastructure around you continues to support the idea of renting it.

and as they sell you continue to 1031 them back into new DSTs or back into bricks and mortar if you're tired of retirement. 

I will continue to expand, and I will continue this path that so far has been successful.

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

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.

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?)