Critique/add to my plan? (Yes, another dreamer)

[trinity1111]

Originally Posted by Amelorn

Re other islands: My logic was that the larger population of Oahu = more opportunities, both corporate and not corporate. Maui was/is a maybe, but the BI and Kaui seem a bit risky. Also, if I am going to take pursue surfing further, that puts Oahu ahead on the recreation end.

Buying a house and being the landlord is not in the cards right now. I have seen what being a landlord actually means, and it's not terribly appealing ATM.

I would not rely on my online work. I am in the infancy of building a client portfolio (as well as building a portfolio of work), and relevant travel industry changes mean that the work flow isn't guaranteed in the long term.

From what I can gather of work, education, lifestyle and recreation, I would suggest Maui. Also, avoiding surf traffic and finding parking to go surfing is exponentially easier on Maui then Oahu. BI, out of the running for everything. Kauai, a bit of a "one-horse town" kind of island IMHO, not enough going on or direct international flights.

[Amelorn]

Originally Posted by Futuremauian

Dave you are stuck on this notion that people like this OP have no chance of getting any work except part-time, low-wage, no-benefits jobs. It is simply not true. For example, he could become a teacher. This year the State is short 500 teachers. Subbing pays $150+ per day with just a bachelor's degree so he is more than qualified for that. There are many other possibilities as well. Construction is booming as is the entire hospitality industry. Someone with two degrees and experience living in many different countries is probably adaptable. Not everyone needs to amass a huge wealth portfolio to be happy in life. Moving here with $100k puts him miles ahead of all the dreamers who come with $10k (+or-).
BTW: While he may not be able to move his belongings here for $25, it certainly won't cost thousands (as you suggest) unless he brings furniture. Not likely!

I am aware of the Hawaiian teacher shortage, and I'd be open/delighted to teach history.

Construction I am wary of due to my unwillingness to take a minor, non-problematic back injury from my younger days (slightly wedged vertebrae) and turn it into a social security disability claim because either myself or the foreman got a bit ambitious one day...

Currently, I am having a final debate in my mind over Oahu vs Maui.