The Openmoko isn't really a phone. It works to an extent as a phone but it's
more like a small tablet. Some of it's features I find to be really cool,
e.g:
1. You can use it without a SIM card at all. The distributions will complain
that no SIM is found but you can still use all the non-phone related
applications like internet and games. Some distributions are not related to a
phone at all (e.g. Gamerunner is a distibutions just for playing games).
2. You can charge the phone by connecting it to a computer connected to a
power source even when the computer itself isn't on. Admittedly it charges
very slowly this way, but at least you never have to worry about the phone
discharging at night if you left it connected to the computer and decided to
switch off the computer.
3. Distributions like SHR and QtMoko can be run directly from a microSD(HC)
card, so backing up data and switching distibutions is very easy.
4. You don't need GPRS or wireless to update the software on the phone or
test applications which require internet as you can share the internet from
your computer via SSH.
5. Another cool feature is the USB port can be used in slave and host mode,
so you can copy pictures from a camera to the phone (admittedly I have yet to
test this myself).
In addition, some of the applications are pretty good. I especially like
Pidgin and FBReader. Evopedia (offline Wikipedia reader) is pretty good as
well on SHR-testing. The software on QtMoko which takes snapshots is cool as
well.
The bad part is that the phone software itself isn't always usable. For
example I cannot receive text messages on SHR and I cannot connect earplugs
on Om 2009 during a phone call. QtMoko however works fine as a phone, but the
Debian repositories are not optimized for the phone, so installing software
requires more effort. Also, some distributions don't come with virtual
keyboards of all the languages so you might need to write a keyboard yourself
if you are not an English speaker.
To answer your question: if you use a distribution running on a microSD card
and back it up regularly you should be fine even when software updates or
installations cause problems.
I actually have the Cambridge dongle and it behaves rather erratically
unfortunately (it sometimes works but usually it doesn't). It might be
because the one I have is faulty (I will test another one later this week).