What are the most web-capable mobile phones to date (models and / or user agents) and
What rules should be assessed when trying to determine if the
What are the most web-capable mobile phones to date (models and / or user agents)
I think you've already identified the most important ones: iOS devices, Android 2.0+, and recent BlackBerry devices. But really, if you want to know how well your site is supported, you should check out the emulators/simulators available for particular devices.
An excellent list of example User-Agent strings can be found here.
What rules should be assessed when trying to determine if they will handle a rich mobile customised site?
BlackBerry devices running OS 6.0 or higher will have a WebKit-based browser which supports the latest goodies, so you could improve your filtering for BlackBerry devices to anticipate new/unreleased devices that will work well. The following User-Agent example shows that the device is running OS 6.0.0.141:
Mozilla/5.0 (BlackBerry; U; BlackBerry 9800; en) AppleWebKit/534.1+ (KHTML, Like Gecko) Version/6.0.0.141 Mobile Safari/534.1+
Prior to OS 6.0, the BlackBerry User-Agent looked a bit different (and the web browser experience was much worse). The following User-Agent example shows that the device is running OS 4.7.1.40:
BlackBerry9630/4.7.1.40 Profile/MIDP-2.0 Configuration/CLDC-1.1 VendorID/105
If the device supports preferred_markup = html_web_4_0
From WUFL