Thanks everyone for the great insights. Regarding AIRDNA & how we're using it. We used AirDNA to try and short-list neighborhoods on Maui we'd like to operate in. Cross-indexed against neighborhoods we enjoy the most to actually spend time in when in Maui.
Went on AirBNB and VRBO and actually used their calendar features to try and validate the overall trends & occupancy on what would likely end up being comps for the property types we're considering.
One thing I've been disappointed in AirDNA about -the "revenue vs mortgage payment" feature to try and identify best cities is pretty weak. From what I can tell they assume all houses in the same ZIP have the same purchase cost. I agree that feature is pretty misleading.
One of the things I was trying to convey (poorly) in my original post is that the # of units available according to AIRDNA has basically doubled in the last 24 months. That's alot of new supply. I suppose this could be just a bunch of management companies finally getting on the AirBNB wagon and not a true conversion from LTR to STR though.
Thanks again to everyone who wrote back I think we have enough data to make some decisions here :)