There are other reasons to keep up with OS upgrades. Many times RIM opens up new API's for 3rd party app developers that require the latest OS's (i.e. 4.2.1 vs. 4.2.0.) If you choose to stay back with old OS's you *may* lose some features in 3rd party apps or even lose compatibility with them altogether.
That being said, have you ever read the Quick Start Guides or the Blackberry Pearl Tips guide that is included in the box with the Pearl? Keep in mind that when a new OS update comes out then TMobile has to rewrite all of those for inclusion in the box. I noticed that dialing letters in the phone app is in that guide. So if that feature has a major bug (like it does) that could be why TMo hasn't released that OS. The 4.2.1.96 is a good stable release but RIM really needed to fix that bug.
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