I had this weird idea: drupal has become so complex, with so many moving parts, that understanding the big picture is like predicting the weather. I forgot how long ago this was, but I know this would have been an accurate report:

PLANETWIDE DRUPAL REPORT [sometime in 2008]

Tornados expected to hit everything WYSIWYG. Should consultants flee to WYSIWYG solutions that will fall into the ocean in a few months? Depends... Some experts say, just hang on to your img_assist, and teaser breaks! Others say, you're gonna screw your clients any way you look at it wysiwygville, get drunk.

Views and CCK are getting much needed sunny whether in drupal 6, but panels better bring its unbrella, because its got a lot of storms ahead.

Have an eCommerce component? Better stay put in drupal 5, because drupal 6 is still in a hurricane.In other news, people staying put in the drupal 5 eCommerce storm risk being abandoned on a desert island to starve slowly.

Also, drupal 5 will fall into a boiling cauldren of lava in two years...

***

Stuff is calming down right now, but does that just mean a drupal 7 storm is coming? What made the drupal 6 transition so stormy was all these key, business critical modules remaining stuck, while new vitially important improvements were being made in drupal 6. When in the midst of a transition between drupal versions, sometimes it feels like that southpark election beteween Giant Douche, and Turd Sandwich. The decision boils down to how you want to cause yourself pain.

There's no good solution, And "encouraging module maintainers to keep up to date" is sheer humbug -- yeah, how bout YOU keep those modules up to date. That said, I feel like there's technology in place that could be used to develop early warning systems for stuff like a drupal update, and at the very least, make drupal version updates something that you can assess without spending hours upgrading, only to find out that you gotta flee back to the old version.