Widget ideas
----------------
Record memo widget - widget screen lets you add a memo, or view waiting memos. Option to delete old messages.

To-do list/reminders - something like RememberTheMilk.com would be great, but it doesn't need to be that complicated.

More ___ of the hour stuff (like the Phrase of the Hour widget) - i.e. Quote of the hour, Biography Channel bio of the hour, Guitar chord of the hour (that also plays the chord if you want it to), auto maintenance tip of the hour...

AskANinja.com - already is Flash...

HomeStarRunner.com - StrongBad emails (already is Flash...)

More IPTV-type stuff - Hulu.com, Daily Show, History Channel "Modern Marvels" clips, etc.

Recipe finder w/ dropdowns so you wouldn't have to type. I think I've seen this mentioned before...

Homeseer controller (smart house) - not that I have one, but I've seen this on other widget/plugin software (i.e. GBPVR)
Speaking of which, access to GBPVR (http://www.gbpvr.com/) "next recordings/available recordings" would be fantastic

Other ideas
----------------
Rotating ads / new feature list on software updates - this space could be really well utilized with ads, as long as it still had a progress bar. Talk about a captive audience...

On-screen popup w/ previous/next/pause buttons for all widgets

Release a "Chumby Developer Kit" with Adobe, both as a free add-on to Flash dev software, and as a low-cost standalone software, that has tag insight to the Chumby API.

Chumby-branded mini USB keyboard, or support for a few keyboards, anyway...

Web browser of some sort - Lynx even :-), or just access to your favorite bookmarks, just for when you need it. Would pretty much require the mini keyboard.

---
I've got more widget ideas that I may want to try and tackle myself - we'll see...