Leasehold STR Properties in Hawaii

[Justin Sheley]

Wondering if anyone on here is successfully purchasing, managing, and profiting from leasehold properties in Hawaii, particularly Kauai. If so, how are you choosing to finance them? We have one fee simple property in Kauai and are working on closing on a second fee simple condo. But I'm continually intrigued by the value of the leasehold properties, but just have such a hard time wrapping my head around if it would be worth it to invest in a leasehold with 15-20 years left.

[Mike V.]

I have multiple fee simple properties in Kauai and wont touch leasehold.  

You can cash flow with leasehold but you eliminate appreciation and finding buyers when the leasehold expires in 10-15 years will be difficult due to the uncertainty.   

I would personally avoid unless your business strategy is different than mine.