I have to admit that the upgrade from 5.12 to 6.8 was not trouble free. I followed the instructions in the 6.8 INSTALL.txt to the letter: I backed up my db and site, and upgraded Drupal core and all contributed modules to their latest versions (actually, everything was already current except for a couple of contrib modules). As a matter of housekeeping I also uninstalled a couple of modules that were not being used.
All went well except for the upgrade to the CCK Imagefield module and to Views. The problem with Imagefield was that I failed to take into account that the 6.x version, unlike the 5.x version, requires the File Field and Image API modules. Even if I had read the Imagefield 6.x UPGRADE.txt (quoted in its entirety here), it wouldn't have told me that Image API is required (issue opened):
Upgrading From 5.x-2.x -> 6.x-2.x
1) If FileField is not already installed, disable ImageField.
2) Upgrade Drupal and contributed Modules to 6.x.
3) Run Update.php
4) If FileField is not already installed
a) install FileField
b) enable both ImageField and FileField.
c) run update.php.Image API is listed as a dependency in the imagefield.info file, which means that you can't install the latter without the former. After I figured that out, I discovered that references in PHP code and templates to the CCK field that I created using Imagefield broke. Basically, you need to convert $node->field_screencap[0]['view'] in PHP snippets and template files to $node->field_screencap[0]['filepath'].
Lesson learned: always read the README.txt, UPGRADE.txt files for any new versions of modules you are installing. Wouldn't hurt to take look at the .info file too.
Now on to Views. Upgrading from Views 1 (5.x) to Views 2 (6.x) requires you to "convert" each view using a simple tool provided in the admin section of the 6.x version of the module. This tool didn't work for me: when I converted, all three of my views produced the same set of 9 seemingly random nodes. Also, the Published filter for all three had been change to No, and the Type filter (all three were simple node listings based on content type) had been unset (i.e., none selected). In addition, the "link to node" option for all the titles used in the views was reset. Finally, the Distinct filter was no longer recognized and had produced the following error: "Error: handler for node > distinct doesn't exist!". All told, I ended up pretty much recreating all three views, so I'd say the "conversion" too is still not very robust, at least for simple content-type views.
Some other miscellaneous problems that came up. Several items in the Navigation menu disappeared, which I put back manually. One of them was the "My workspace" link, which I cannot put back. I've filed a support request on this one since attempting to manually add the menu item results in a (legitimate) error.
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Detailed 5->6 upgrade guide
This is worth checking out: http://becircle.com/how_upgrade_drupal_5_drupal_6_steps_3_and_4_actual_u...
Not surprised.
I had similar experiences with the Views upgrade. It wasn't pretty and required a lot of manual cleanup, but to be honest ... I love the new interface. In the long run, I've come to consider it completely worth it, though in the short run I was not a happy camper.
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