Difficult to "island hop & move around" if you've committed to buying a house and end up with the neighbors from hell.!
If you're asking what properties you need to build - you dont really know your market do you Mr hobby developer? This post was about affordability for US$5K pm - he can live well and only ever need commit to a annual lease - job done.
Who in their right mind wants to buy a house on land they can't own? The whole Asian property market is massively over valued and the Peso has lost value consistently this year. Why 'import' large sums of capital into a corrupt system where even the Banks will only guarantee 500K Peso? As for foreign condo ownership - just Google all the crap owners have to content with there and you will soon get the real picture lol.
My dear original poster. Enjoy your US$5K pm. You only need about US3K pm in most provinces to live handsomely without worry. If your health ever fails - you can simply LEAVE with nothing more than a car/bike/belongings to sell - KEEP IT SIMPLE.