Torch, I'm obviously not going to be telling you anything you don't know since you recommended a lot of these to me anyway, but here's my list:
24term - handles both serial and TCP/IP, seems to display my favorite BBS's most accurately of all the other ones I've tried, open source!
Total Commander - I really like the double windows, direct registry access and shortcuts
MS Plus Network Utilities - for the IP address check, although ping doesn't work very well. Need to find a better program for this really
Battery Monitor - I like always having a quick readout of what the battery % is in the taskbar
OKey - especially on the MobilePro, to re-map the arrow keys to a sensible arrangement
SoundWidgetPro - also on the MobilePro, for mute and volume control without drilling into Control Panel
Small Tweak - gotta have this to fix the ridiculously large fonts and scrollbars
Various games - Need my games to go! mille bornes, stratego, risk, various card & board games
Warehouse Guy - Sokoban gets a special mention
HaaliReader - love having dictionary functionality; great program for text based files/books; it has themes for reading books for a long time
Tombo - best app for hierarchical information organization; I like how simple but powerful it is
Winampaq - I like that it supports winamp themes! Here's a rabbit hole for you:
https://skins.webamp.org/
Other things I use/find useful all the time:
HexEditor
Executability Check
Things I'm still looking for/evaluating options:
-Network utilities
-Financial tracking program
-File/disk encryption utility