Thanks for the replies everyone! As always, the bigger pockets community is awesome!! @Patrick Franta yeah I'm tracking the taxes and HOA fees separately in the worksheet I provided. I'll be self-managing so I added $100-$200 a month for my on-island agent fee. As for the 14.5% TAT/GET, if I use VRBO for my bookings they will collect that from the guest directly. As far as I can tell Airbnb does not yet offer that capability in Hawaii.
I met with a few agents and cleaners while on island and their feedback was that it should be cash flowing nicely without any major repairs or upgrades. We do plan to make another trip out to redecorate and move a few things around after closing -- little things to increase appeal.
It sounds like inventory is pretty fixed in the Maui short term rental market, but I'm not sure if that's a safe working assumption for the long term. I guess tourism is an important enough industry there that while they need to limit the short term rentals for local residents, they also need them to provide lower price points for visitors. Is there any concern that the local government would ever ban short term rentals altogether?
Of course there are always 'what-ifs' so you can't get hung up on those. We're planning to moved forward with the purchase and appreciate all the feedback and suggestions.
@Loren Clive yes we are looking at several options for an on-island agent. At this point in time it seems like it will be most economical and convenient if we use the same provider for cleaning and on-island agent. We plan to go the most cost-effective route initially, and then adjust later as we build more experience/reserves.
Thanks again for all the great feedback!
-Rob