I've been a wireless@SG user for about 2 years now and found it to be convenient (if somewhat occasionally flakey) as a frequent traveller to Singapore...
I also had problems initially registering... Gave up with Singtel and Qmax... but eventually I managed to sign up successfully online through icell with my Australian passport and a prepaid Singtel number.
(I say its flakey as sometimes it hasn't allowed me to sign in at the airport giving some error message but usually when I try again on another trip it works... never bothered to contact the helpdesk to find out why)
I'd also recommend getting a prepaid 3G broadband for those times you can't find a wireless@SG or for use in your hotel (or both!).
I haven't tried the M1 offering but StarHub now has a new flexible offering if you have a 3G modem or a 3G phone that you can dedicate to tethering (the sim card doesn't allow calls but you can sms).
Otherwise StarHub also sells a kit for $SIN99 which includes a Huawei E1550 HSDPA usb modem plus a $SIN18 sim card with starting credit.
I picked one up at the UOB Forex place in Terminal 3. They took my passport and registered the sim card for me and it was ready to go!
It seems a very good price especially considering the included sim card and credit and the also fact that the modem isn't locked so you can use it elsewhere! (It is cheaper to purchase a usb modem in the Philippines but those modems are locked which you have to pay to get unlocked)
The software is loaded from an virtual disk image on the modem itself.. It worked pretty much out of the box on my Macbook and also in Windows.