Doug wrote:
Highly unlikely you will keep the plane for 40 years. Practically
unheard of.

One more reason why the mainland is different from Hawai'i... Two guys
at the airport have had their Cessnas for the better part of 50 years
now, one guy has a Cherokee Six he's had for 30, before that he had a
Piper cub for 20. Lot's of Beech Volpars are still in service with the
same people (or their grand-children) with which they were in service
beggining in the 30s, while one cargo airline (Kamaka Air) flies DC-3s
that it had fully restored, which I believe were old Trans-Pacific
(Aloha Airlines) DC-3s.

I would recommend buying a single, non-retract airplane that will carry
the load you need to carry. Cessna 172 or 182 or a Piper Warrior or
Pathfinder. Retractable gear is a maintenance headache. With your short
hops, speed doesn't really matter. I would also recommend buying it
with the avionics you want, although with 10K in shipping costs you may
have a hard time finding exactly whay you want in Hawaii.

Call me fickle, self-oriented, greedy, snobby, what have you, but I do
not fly and will not own a fixed-gear plane.

As for leaseback, a simple plane like a 172 or Warrior will rent MUCH
more often and the required insurance premium and required 100 hour
inspections will dictate that you rent it as much as possible if you
want to have any hope at all of breaking even or better.

Yes, but it will rent to people who wil bust it up too, I'm not looking
for volume, I'm looking for people who are willing to spend a bit more
than they normally would to get a premium product, which I can think of
at least 4 already.

If I were in your shoes I would either get a 172 or a 182, one of the
later models (1999 or so), but not a new one. New airplanes depreciate
a LOT the first year, so I'd let someone else take that hit. However an
older model that has the avionics I want, if I can find it, would do
even better financially, but would not have the newer planes
reliability. If you prefer the Piper line, then choose one of those.

No fixed gear, I would entertain a 182RG, but the 235 HP engine puts a
big bump up in that insurance over the 200 hp one in the 177 and the
Arrow, also I in particular dislike 172s for their stall
characteristics, they seem to break quickly and fall rather than stall
out.

Good luck.