My name is Mike Gallagher. I own my own Brokerage here in Kailua, Hawaii on Oahu and although I realize my answer is some what delicate, the reason most folks buy Lease Hold Property is that they are elderly, are not concerned with leaving any equity to anyone, not concerned in Selling and upon their expiration its a "Who Cares?"
If you really want to know about Hawaii Real Estate, visit my website at http://www.hawaiirealestatestatistics.com or http://www.aroundhawaii.com under "Real Estate Articles."
I am currently looking at taking over a coffee farm in south Kona that has a very short term left on it's lease. Initially I was concerned, but with 2 years of research, I am now much more confident to move forward.
Those looking at property in Hawaii have to decide what is right for them. There are advantages on both sides of the tenure argument. Talk to the pros like Mike and Erik, and people that are living on both property types and follow your gut.
Just a note: What you're describing is not a lease-option, as Tim believes. It's a leasehold--quite different. Sounds as if you've encountered a bad one. Not all are bad. Some are written for long periods of time--such as 99 years. In the interim, you can sell the property. Some properties in Baltimore are like that; in some cases, you can even pay off/buy (not sure of the exact terminology) the lease for a relatively small amount.
But 14 years is way too short. There's a reasonably good chance you'd still be there. And if you couldn't renew the leasehold for a minimal amount (which, from your friend's comments I'm guessing you couldn't do), then there wouldn't be much advantage. The only possible advantage--not enough to outweigh the disadvantages--might be the deductibility of the taxes you'd be paying. (I'm not an accountant, so this isn't financial advice.)
Again, while some leaseholds do make sense, listen to your attorney friend. Sounds like very good advice.
Hope that helps.