For your "wobbie" the Wiggy's are great, I have two along with my original liners. A Sungpac Softie3 is probably about the same size and will be more comfortable if the temps drop however.

For a AA light...

http://www.zebralight.com/SC52-L2-AA-Flashlight-Cool-White_p_136.html

...most impressed with mine. Running it on a 14500 and the difference to a AA is noticable.

There have been a lot of great recommendations in here. I haven't forgotten this thread - I've just been sidetracked.

AZ,
I have quite a few of those Mini-Mag carriers laying around, but need something about the size of a roll of quarters for daily use. I wear dress trousers to work and like to "pocket clip" the light into my off-hand rear pocket.

For my general use bag - I like your suggestion.

Randy,
Diamonds always worry me. I don't want to be too aggressive. I've stayed with ceramic and stone but for quick edge establishment I can see a diamond pad being the way to go.

Andy,
I didn't know about the Softie3. I'll have to look into it. My new backpack is smaller than what I was using and space it at an extreme premium. I might not even be able to fit a woobie inside.

Take a look at Zebralight for both your headlamp and flashlight. Prices are in the $60 range and the will perform as good as anything out there with customer service that is only rivaled by Surefire.

Their user interfaces are excellent, too.