Spending 2-4 weeks on each island, how would you do it? (Honolulu: environment, real estate)

[Think!]

I'm considering a move to one of the islands from the mainland and would appreciate some guidance.

I'm planning on flying out mid-August and I'd like to spend some time living on each island (two to four weeks each) to get a feel for each one before committing to an extended trial and eventually a move once real estate values bottom out.

My current plan is to pursue room rentals which would allow me to benefit from the experience of the person I'm renting from, as well as provide a decent value while I explore each island. Does this sound realistic?

I operate my business remotely via the internet (I will have a laptop) so high speed internet is a necessity and local employment opportunities are not even a consideration. I'm pretty flexible about where I stay and I actually prefer to be slightly removed from the bustle of more urban environments.

If I were a close friend of yours, how would you direct me to engineer this visit for maximum exposure and value?

Anything I should look out for? Scams?
Must-See?
Order of visitation suggestions?
Is 2-4 weeks enough time?
What would be the best way to secure transportation during these visits? TheBus?

Thanks!

[MadRussian]

If you going to spend few month on Hawaii, it make sense to buy cheap car.

[jenalove]

Would just rent a cheap car on the outer islands, not necessary on Oahu (can take the bus there). I would use vrbo.com and rent a few different places on each island for a week at a time. On Kauai, would stay in Princeville area and then Poipu area. On Maui, anywhere on the west/southwest side (Kihei, Kaanapali, Wailea area) and then somewhere upcountry (haiku, pukalani, kula area). On Oahu would stay somewhere south, maybe near Honolulu and then somewhere more on the upper east side. On the Big Island would stay on the West side, Kona area, and then the volcano area (but just to see the volcano, not to live there). Hope you get the chance to really do this. I have an internet job too, and my husband is working on getting one so that we can move anywhere - Hawaii is my #1 choice! So far we have narrowed it down to Princeville, Kauai or upcountry Maui, but still looking. We are not looking to buy, so that makes it much easier for us. Please do report back on your findings.

[jenalove]

PS - I would just start with the Big Island and move west from island to island. It's just a short flight to each island.

[whynot?]

You might want to start looking at the local papers online, too. Even just reading the Honolulu Star-Bulletin and Honolulu Advertiser will give you a sense of what's going on locally. Each island has its own local paper, too, and they give you a real taste of what's going on.

[Think!]

Thank you for the insights into the areas and the tip about the local papers - I hadn't thought about the papers! Happy to hear about your work on the internet - it's wonderful the freedom this medium can provide.

[Ellwood]

Motor scooter would be enough for transportation for you. If you wanted to travel all over the island, rent a car for the day.