I'd think long and hard about giving up UMA. If you do, make sure that whatever replaces it has adequate coverage and that you've got enough minutes. Personally, I'm waiting to see if an Android with UMA materializes in the near future (there are rumors). Absent that, I may get a Blackberry 9700. Worth a look, anyway. Again - this is predicated on whether you need UMA or not... and whether you're grandfathered in on some of the older and far less costly TMO plans.

As to the laptop, I'd lean towards a Macbook, maybe with an external monitor. Get Applecare and put it on an Amex that gives you an extra year on the warranty. You'll be set for four years. No dealing with crappy updates, virus scanners sucking up the system, etc. Sounds like you don't do anything that requires Windows. FWIW, I don't have one, but my kids do. I switched them after they managed to repeatedly get their machines infected with all sorts of stuff (even with an updated virus scanner, spybot, etc.). Only issue is that I've got so little sysadmin to do for the Mac I keep forgetting how to do stuff.

Lastly, I'd keep the ipod apart from the phone.... at least until Apple provides an additional battery. I'd hate to watch videos all day and then not have enough juice for a call.