Hi GLENN,
Firstly I will admit that I admire both your aspiration and your determination.
Unlike many, I think it's perfectly possible to live the kind of life you outline, provided you really want to, that it will make you happy, and you know just what it will be like.
I would guess you already know that the biggest things that can bite you are medical
(you and your extended family) and any emergency needs to return home.
If you feel the need, think about insurance.
Regarding finances, may I very kindly suggest you consider something like HSBC premiere account (offshore). Take a look at the benefits it offers you living abroad.
I believe there are many more experienced members can offer advice about immigration control and requirements in Phils. Please do a search, google it whatever.
Understand, that it is not diificult. Yes, there is red tape, but really not any problem.
Many many people have done it before you. The Phils immigration site has plenty of info.