Maui vacation rental vs. long term rental

[Brandon Rollins]

My wife and I are strongly considering buying a Maui rental property early next year. The areas I’ve been studying are Kihei and a few different resorts around Lahaina. I’ve spoken to a couple different realtors, but all I get from them is ,”this is a great buy.” I’d like to be connected with a numbers driven individual who could help steer us towards something that isn’t a cash flow disaster.

Questions I would have.

What’s the typical premium paid for a short term rental? Is the view worth the 100-200k?

Are we better of working through a local bank?

What complexes are known for having the best short term rental managers? How do you know if a unit has a special assessment looming? On and on.

I’m not new to real estate and helped my father buy and finance two properties on Oahu in the 2003 which he subsequently 1031k’d out of.