Stefan,
For the first tests I used the SqueakVM 3.0 compiled for ARM (http://www.is.titech.ac.jp/~ohshima/squeak/WinCE/) and a default 3.2-image. Everything seems to work fine, i built funny buttons, lists and so on. Networking works fine too (WLAN).
The VM was from 3.1alpha. It doesn't have some newer features, but for 3.2 image it should be fine.
I'd like to know if there are any pitfalls - for now everything seems to be a bit too easy.
Yes, if you're willing to write your own buttons, etc. Squeak is perfect.
Do you have any hints/ tips for stripping down the image?
It is a try and error process, but you wouldn't have to strip it down too aggressively in this setting?
Any ideas on how to implement an automatic installer (an executable that installs the sw on the iPaq)?
I'd like to know the answer for this, too^^; There must be some.
I heard of the possibility to "close" the image (prevent the user from opening a world-menu etc.).
Ned Konz has a package called Lockdown.
http://map1.squeakfoundation.org/sm/package/0c6d3bda-adbb-496a-ae84-8d4c145d...
I don't know how applicable it is to the 3.2, but should help.
Of course, if you go to the full-screen mode, and ah... if you re-compile the VM with different #define macros so that keyevents get reported to Squeak, you can make it really "closed".
-- Yoshiki