Electricity is as you say extremely expensive in Manila and second hand cars are stupidly expensive it's a sellers market over there I guess.
You can get a 50 year lease on a property such as a condo but as you say you can't own a house without some very fancy legal shenanigans to ensure that you have the right to live in it and to dispose of it as you choose, it can be done though just not easy. Same for owning a business you have to get the rights assigned back from named locals, I know of two software companies that are set up this way.
I don't know any upper class Filipinos, I do know one middle class guy that works for ebay and earns a western style salary (still low but very good) I also know a number of very educated Filipinos who earn about 300 quid a month two of them lawyers and one a computer programmer and they are all very decent people, the rest are poor, some of them have motives for being friendly but many of them don't and are just good people.
I'd do it, manok and rice, electric fans, pinoy tv, jeepney's don't scare me, that's pretty much our life just now when I'm there
(the living room in the house we rent is huge and I could never afford to air condition it
)
I also have no problem with going out to a local pub rather than a fancy restaurant / pub / night club in Malate or Makati, there are lots of cheap places with good music that we like to go to.
I would need an internet connection though that would be essential if I were there for a long time.
What does scare me is women in combination with shoe shops and malls and that's the main reason we'll be staying here for a good long time once I finally get Ana and the kids over here
Jim