Some thoughts :

- Upgrading to Zope 2.8 without reading the release notes.
I followed the release notes but this didn't fix catalog errors. I am not the only one. This is apparently fixed in Zope 2.8.2 but that doesn't look like it can be downloaded yet.

- Third party products that are not yet fully compatible
  with Plone 2.1 and/or Zope 2.8.
Should this perhaps be the other way around? If those products used the APIs correctly, perhaps a new release of Zope/Plone should still support old APIs and/or deprecate them gradually and with warning? This is a difficult problem to address but sometimes it may be better to hold back on releasing something new if it causes things that depend on it to break. On the other hand I can understand peoples desire to release something new and cool (even if not quite ready) . ;-) And its hard to know quickly what the bugs are if you don't release it to the real world. So hard to know what to do..........

- Sites that have customized parts of Plone they shouldn't
  have touched in the first place.
This is an important issue. It is difficult not to touch things that one shouldn't. A trivial example - If you want your breadcrumbs to just list the breadcrumbs instead of say "you are here" you have to copy across global_pathbar.pt and take out "you are here". There is not another easy way to do it that I can see. If you then migrate to 2.1, that .pt has changed so you have to copy the new one and re-do it otherwise nothing renders. If you want to add another logo on the right of the header you have to hack Plone's templates further. Each change is in itself trivial but they add up and when you migrate, you;re left with stuff that doesn't work and spend quite a while resolving it. And thats for those of us savvy enough to use the filesystem. Those who customised through the ZMI will have a bigger headache.

as for the broken products, that is a pandemic within the open source community, hardly unique to plone.

AT's problems are entirely recognized by those of us who use it heavily, and i can assure you that the AT developer pool has no intention of continuing to pile more cruft on top of a shaky stack. . the first iterations of this will probably also have some warts. but please don't assume that plone/AT developers don't see the same problems that you see, and that they aren't willing and able to learn from their mistakes.
It would seem Archetypes has improved over time.

My real worry is when we do have a new release of Plone sitting on top of Zope 3 we'll have a whole new set of bleeding edge code sitting on top of other bleeding edge code, while stuff that did work with a mature AT1.3.x (or 1.4.x or whatever) suddenly stops working.
Hopefully this will prove to be an unjustified fear!

Probably this is no-one's fault. It is the nature of open source. To compare, have to admit I tried to get Bricolage to work a while back, and ran into CPAN dependency hell.

I wonder if perhaps the real problem is trying to do so much with so few resources. Linux has a very mature platform as much of its base, and a lot of commercial support which helps. Perl and the CPAN is quite mature now and also had quite a lot of commercial support. The good thing about commercial support is people being paid to do grunt work and run loads of tests and update documents. Both Linux and CPAN are very modular. It is relatively easy to change one part without knowing about other parts. I think it would be easier to find someone who could patch a broken CPAN module, than someone who could delve inside Zope and Plone. This is because many of us don't understand the various components of the underlying architecture, and a lot is changing for Zope 3. Also many Perl modules are widely used by many applications, whereas a lot of Zope code is only used by other Zope code.

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