OK, it looks like I'll be there around the New Year. Tentative plan:

Couple of days in Hong Kong
3 days in Bangkok
Take International Express train to Penang, overnight stay, arriving in Singapore
Couple of days (1 night, see below), return to USA

I've found reasonably priced places to stay in Hong Kong (JJ Hotel in Wan Chai, ~$110 USD a night, Amari Residences Sukhumvit, ~$80 USD a night, Banana Boutique Hotel in Penang, ~$75 USD a night)... but I am totally striking out on anything that looks decent and is under $150 a night. The stuff I am finding is Hotel 81's in Geylang with a bunch of mixed comments.

Do my expectations need to be radically adjusted? Is waiting for later on better (wotif.com is too far out right now, but it looks like they have some interesting deals)? Is Pricelining/Hotwiring going to help? Is there a B&B someone could recommend?

Anyways, yes, I'm cheap when it comes to hotel rooms (though not hostel-level/couchsurfing cheap, though I'll stay in a pension with shared bathroom). I like finding good "sweet spots" of cleanliness/convenience/pricing/value; sure ,marble appointed suites are nice, but in the end it's a place to lie your head; the real excitement is where you are, not in your hotel room. I find it interesting that in 3 trips to Hong Kong in the past, also a rather expensive city in Asia, that I've found hotel rooms in Central for ~$100 each time, but Singapore is...well...priced pretty heavily, and my usual methods don't seem to work (though if I can pile up some Hilton points, it looks like cash and points at the Hilton Singapore could work).

Any suggestions?