Round-the-world 5 stops allowed - econo trip suggestions? (cost, rent, hotel)

[StealthRabbit]

I need to burn through some UA / Star Alliance airline mileage and am considering doing a 'R-t-World' (200k miles or 300k 'business-class', Benefit when checking in + 'guest lounges')

Looking for economical and convenient 'hubs' for nearby destinations.
I might rent a flat in various places, or will be trying to stay in 'guest-homes' (~$20 / night, as I have for ~ 15 yrs)

I think I will plan a 4-6 month trip starting in Nov (09?)

I'm allowed 331 days and 5 stop-overs & 'open legs' allowed (ex. can fly into Frankfurt and out of Madrid). I would like to use award travel to get to destinations I will not be able to afford again.

I've lived in Singapore, Spain, and Canada (BC) and currently in PNW.
I do want to spend considerable time in Asia, and Europe, but not sure about SA.

Any input?

Cost per day? (would like to keep under $100)

Routing / timing
I hope to go 'Micronesia > NZ > Singapore (stay for a spell and travel Malaysia / Indonesia / Thailand / Chinese New Yr) then
Singapore> Bombay> Eastern Europe (land travel throughout Europe during Spring 2010)

then depart for SA (Argentina / Brazil / Chile / Bolivia) and back to PNW in time for our nice summer.

Hubs - ? ez places, econo hubs, ''do-not-miss" - EXPENSIVE places to avoid

"trekking ventures" ? side trips not to miss

other ideas? budget - couch surfing, econo eating, travel via 'night train/bus' to save hotel expense. Discount seasons, packing for economy.
cheap ground transportation ideas.

my general thoughts... travel / sleep / eat, like the locals