Drupal 5 Or Drupal 6?
Ever since Drupal 6 was released people have been wondering whether or not they should upgrade from Drupal 5. Meanwhile people who are new to Drupal wonder whether they should start their site on the 5 or 6 branch. These questions are valid. I've asked them myself. This site is built using Drupal 6 but I still have a few others on Drupal 5. Having a bit of experience using both versions I'll do my best to shed some light on which choice you should make.
To Upgrade Or Not To Upgrade
You'll find the answer to this question if you do a simple analysis of the contributed modules that you have installed. If you have a pretty simple setup with few contrib modules then this task will be easy. Check your modules with the current versions on Drupal.org to see if the modules you are using have a version for Drupal 6. If all do then you're one step closer to upgrading. If only some do you then have to decide whether the functions are critical to the operation of your site.
The choice is tougher for more complex Drupal sites. The process is the same as the one I have just mentioned but you will spend more time evaluating modules. Take your time. There's no need to rush to a hasty conclusion.
If you do decide to upgrade then the next step should be to take a closer look at the support queue for each module. If other people are having problems on the 6 branch it might give you second thoughts. If you still feel comfortable after checking the support requests then consider setting up a test site prior to the upgrade.
The test site can help you accomplish two critical functions. The site allows you to become familiar with the new functionality and processes in Drupal 6. And it also gives you time to test upgraded modules. Test test site approach takes more time but greatly reduces the chances of ending up with a site that doesn't function well.
Which Version To Start With
If you're new to Drupal this question is a bit more cut and dry. If the needs for your site are very simple, like a static corporate website or a straight-up blog website then I think you are fine to start with Drupal 6.
If your website needs are more complex then you have to think about it a little more. Full blown community sites with user-generated content are more likely to rely on modules that aren't 100% ready for version 6 yet. You will probably be better off starting out on version 5.
If you have a bit of runway before you need to launch your site then version 6 might work too. You can get started configuring the more basic modules, tweaking your theme and organizing the site. It's a good bet that most, if not all, of the contributed modules you will need will be updated given a bit of time. Take the advice in the previous section to assess the situation.
So if you're in a crunch to launch a feature rich site then by all means go with Drupal 5. I do recommend that you budget some time to set up a Drupal 6 test site to continue to assess the situation with functionality for Drupal 6.
Speeding Up The Process
The process of progressing from Drupal 5 to Drupal 6 is facilitated by the support of the community. If you have the time to do anything with Drupal 6 you should spend some time over on Drupal.org, providing feedback to module developers on what you're experiencing. And if you're a developer I'm sure that other module developers wouldn't mind if you offered support in porting module code from Drupal 5 to Drupal 6.
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Views 2, CCK 2 and Organic Groups now have release candidates for Drupal 6. These three modules were probably the most anticipated by developers looking to migrate to or start with Drupal 6. http://drupal.org/node/277856
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