Since you're able to update to the newest version of Android, what smartphone is the most well-rounded and has the drivers to update to the newest or close to newest version of Android?
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The short answer is that the Nexus phones are the most updateable - not only do they get more updates then the other phones, but they also get more support from the community in general. Case in point, though Google has announced that the Nexus One will not get ICS, CyanogenMod will be providing it.
Other then the Nexus phones, I think it is best to stick to the high volume devices, particularly the flagship devices that are sold in many countries. These are much more likely to get the attention necessary to push the manufacturer to release updates and to release the drivers.
And finally, you can look at the CyanogenMod list of supported devices. I tend to check this list before buying or recommending a new device.