Its money well spent land development is high risk high reward.. depending on Jurisdiction. 

Are their listings detailed with good-quality photos?

It depends on your financial strength, the quality of the property, how many properties you own, etc.I like to start with one significant expense and three months of vacancy.

Lei, I'd be happy to serve you any way I can.For Ko'olina, I love the Beach Villas (as well as the entire Ko'olina area) and if you are primarily looking for a very quality property for you and your family to use, I'd recommend it.  

Toss in a month or vacancy, a high repair bill, a remodel or what have you and they are making just as much as you are. 

I'm curious about the size and quality of a house you could build for $375k. 

I agree that pricing a rental too high is a classic mistake than can make it sit, but don't you think encouraging landlords to rent quick will make them compromise on the vetting of the tenants?

My income doesn’t show itself as being very high, but I have a relatively large amount of cash to put down.

Highly recommend @Lien Vuong she commented below and has helped a lot of our clients start of expand their investment property portfolio. 

They wrote me Commercial policies with high limits....only $100 mo roughly, never had a problem.I would just ask the company that handles your current home's insurance....some will do STR insurance, some won't.