Tim, welcome to the forum!
I think your idea is sound, but as Steve suggested, it might be easier to try to match a skid steer to a job rather than the other way around at first. You may want to figure out what you'll be doing -- given that you're in Hawaii, you obviously won't be moving snow. However, given the city you live in, perhaps you'll run into rocky soil or clay, in which case you'd want a larger machine (possibly). But the important thing is to have an idea of what you'd like to do... be it landscaping, heavy digging (pools, foundations), or just whatever comes your way. If you choose the latter, I would urge you to go away from a CTL as they're somewhat specialized machines... I wouldn't start a business with one unless the weather absolutely, absolutely supports it. remember, CTLs have higher maintenance costs, are prone to track wear (expensive tracks!), and are designed to be used on asphalt/hard surfaces all day.
Other models I'd consider in that size class are the Bobcat S250; Cat 252B/262B; Case 440, 445, or 450; Deere 325; or Gehl 6640/Mustang 2076 or 2086.
Of those, for a starting business, I think the Case and Cat will be easiest for you to learn on (unless you already have experience). However, as Steve said, you'll want to get a look at hydraulic performance as well. Finally, dealer support will be key, especially in your area.
Good luck and keep us posted!