...which I have pulling out steadily since upgrading from a BB 7290 to an 8800.

First, no matter what I tried, my computer won't recognise my 8800 when connected with the USB cable. So I figured I would connect them via bluetooth, and the frustrations mounted.

I activated my PC's bluetooth scan, and lo and behold, it found my 8800. However, when I tried to connect the two, the message came back that I needed to enable the dial-up connection option in order for the connection to go through.

Whaaaaaa?

So I enable the dial-up option, and, of course, it asks for a phone number. Why does it need a phone number to connect to a Blackberry, and what am I supposed to resond with?

First, if your computer won't recognize the USB something is wrong. Moving to Bluetooth may or may not help. You need to use the Microsoft basic bluetooth drivers in Windows in order to use BT with the Desktop Manager. Once connected with those drivers and not the BT manufacturers drivers you should be able to connect in Desktop manager via bluetooth. There are some threads out there about doing it. A quick search may yield some good results.

What is the issue with USB? (Edit: nevermind, I found your other thread.)