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That depends on if the phone on that line is still working great and getting the job done. There should be some pretty hot phones coming out 1st quarter of 2013, so that just depends on how long you/he can wait.
Nothing has been really announced yet but after a line of power house devices get released like what just happened, generally a few months later another batch of power house devices come out.
Currently though, if he likes the solidness and physical feel of the DROID X, I would consider a DROID RAZR HD/MAXX HD, solid phones that both get great battery life and you should be able to get a decent price on those, last I checked I think upgrade prices were $50 less than normal for whatever promotion they're running. If the HDMAXX HD is too big, the RAZR M is slightly smaller and is also a great phone, and can be had for $50 right now I think, but doesn't quit have the power house status as the HD/MAXX HD.
There is also the Samsung Galaxy S III and the Samsung Galaxy Note II, both of which are solid phones but also physically large as well. I would have him play with the phones at the VZW store and see which ones he likes.
I'm a Motorola fan, so I am a little biased towards the Motorola phones, but the RAZR HD/MAXX HD are solid phones, they don't feel like cheap plastic like some of the Samsung phones do and it will be quit the upgrade coming from a DROID X (which I used to have as well and loved).