We're using Proper Insurance for our VR's.  

Short term agents call us and employ heavy sales tactics to get us to list as a VR, but we ran numbers and don't see it as a viable model, but that may change. 

So even though it is 10% commission the inspectors/handymen will be costly when you add up all their service calls for guests issues/inspections etc.Vacasa(largest VR company in the nation) may service your area as well as Turnkey Vacation Rentals(my previous company).

They both have been long terms rentals in the past but i found that vr is better and the upkeep is better. 

They aren't making any more Earth, and until they do, it's a finite commodity.Earth, the one thing government and the Federal Reserve can't print more of.And for the futurists out there, don't worry in 20 years we're all going to be living off a Basic Universal Income and be living off of robotics and AI.See you in the VR world, my fellow freaks and geeks.

There are deals for LT anf VR in Hawaii, but sharpen your pencil and do the numbers...https://www.biggerpockets.com/blogs/8050/48883-buy-a-hawaii-vacation-rental-and-have-it-pay-for-itself-unicorn-alert

As suggested, search the VR platforms to find other places in the vicinity of your place and look at their photos and prices to get an idea of how you can price your own place, and then assume an even lower price especially as you get started and try to build up good reviews.

A few bits of info: 1) I’m a newbie at real estate investing (though I’ve purchased 5 of my own primary residences over the last 20 years), so I’m not new to real estate purchasing all together). 2) Trying to decide if I should make my first investment deal this VR, or start smaller with a turnkey property in the $80K range. 3) This VR comes fully renovated and furnished, right on the ocean. 

We get this exact question in our little VR community about 3 times per week and it’s always the same answers.

I am looking for a property that can be a full fledged VR, so yes that's my concern as well.