Aloha @Christopher Jordan - congrats on selling your business. And just an fyi - you are not required to have on-island management. If you own investment real estate in Hawaii but do not live here and want to self manage, you are "supposed" to have a "point of contact." I have quite a few clients who self manage their vacation rentals from the mainland.
Here is info directly off state of Hawaii website pertaining to vacation rentals (bold in mine):
If you’re off-island, you’ll need to designate a local contact who resides on the same island as the transient accommodation. The local contact may be an individual or an entity with a principal place of business on the same island as the property. Because they are on the same island as the transient accommodation, the local contact may be able to assist with issues which may arise relevant to the transient accommodation. The on-island local contact doesn’t have to be a licensed real estate professional, unless he/she is also involved in real estate activities, like renting or offering to rent the property.
And I've had at least one client do cost seg - if you'd like a couple referrals, you're welcome to contact me directly.
Lastly, have you considered O'ahu for a vacation rental? I have a couple clients that own 2 BR units at Waikiki Sunset - one of them recently told me he is grossing close to $15k next month. The other client has told me he consistently does $10-$14k/mo. Units have recently been selling in $900-$950k range.