Leasehold property worth it?

[Michael Irby]

I am hoping I can get some advice from experienced Hawaii leasehold investors. I have lived in Hawaii for many years but now that I’m a traveling healthcare provider, I am off island more often than not.

When I’m not on contract I would love to have a place to return to and when I’m away I would love to rent it out for some additional income.

I am very familiar with the strict zoning laws for Hawaii short term rentals but most Waikiki apartments are either too expensive or leasehold only properties. 

Is it worth it to invest in a leasehold? Is it just throwing away money when the lease is over? Help! 

[Michael Borger]

As you indicated yourself, it's mostly throwing away money because you have nothing left at the end of the lease. It's a steady march to zero. That being said, I've flipped leasehold condos before- both by keeping them as leaseholds and by buying out the fee. But you're talking about keeping it yourself, which is a different analysis. Still, I think you'd find it difficult to find one that would be a good long-term investment unless you had another ~20-30 years to go, it's at least cash neutral, and you don't plan to hold it too long (to avoid too much investment loss and before you get to the point where it's unsellable because of too few years left); that's another way of saying that maybe it suits your cash needs in the near-term or is at least less of a pill to swallow than other options until you find something that's more of a sensible long-term play