The reason some phones are not updated past 1.5/1.6 is due to a combination of:
1) hardware limitation - 1st gen android phones don't have a system partition size big enough to accommodate the newer and bigger OS revisions. This was probably an oversight during hardware design and is no longer a problem with the coming phones.
2) The carriers in Canada would rather sell you a new phone than to give users free updates and features.
With that said, you can always "root" the phone and install unofficial updates as you please. (Similar to "jailbreaking" the iPhone). For example, my HTC Dream currently has 1.6 installed, eventhough Robbers never made it past the now obsolete 1.5.
The Moto Milestone from Telus is currently the best Android phone avail in Canada. (Basically a rebranded Moto Droid for North America network support)
Posted via RS Mobile