Hi folks, this question is specific to Hawaii realtors. Please do note I have STR operating in Kailua, so my dream is to invest in multiple island for small condo/STRable property VS I continue expanding in Big Island only. I am also aware about the regulation. The purpose of the STR is for me to able to stay in different island every 2 3 months or so and while I'm there, if I'm not there I would Airbnb, so I generate these pro-and-con. Long term Plan is to retire either in Hilo or Maui ; Hence some questions :

1. Is investing in multiple island common ? lets say I have on STR in Big Island, one in Oahu and one in Kihei /and/or Kauai ?
2. Or is it better to just expanding in one island ? I can drive in island now without maps 
3. I need to park one car in each island, Waikiki has cons that it's almost impossible to park for car and condo unit that has parking space is not always available. The pro is that entry price is much cheaper but less appreciation.
4. Maui is the best island in term of white sand beach but condo entry price is double than BI (800k vs 400k) and area is too commercialized/more expensive than BI. The Pro is appreciation is super good. I kind like thinking Kona / Waikoloa is the net Maui in developing.
5. Kona/Hilo is sort of market where it's still an island, but basic infrastructure is still available. This island has everything while still functioning like an island.

[ personally to retire I prefer to stay in Hilo or up to Hawi / Waipio ]