shallow - 8:16 pm on Jul 4, 2010 (gmt 0)
The WP plugin system is quite a bottleneck for getting people to upgrade. Often the core functionality of a site can depend on a plugin or a series of plugins.
So, when the CMS gets updated there is quite a risk in upgrading, as it might spoil your whole site because some plugin does not work with the new version.
I'm very reluctant to have my web developer upgrade to 3.0. I have full faith and confidence in my web developer but almost every time he's updated a plug-in something breaks. In one case, I spent over 300 dollars for him to set up someone else to come in and find a fix, and it's only partially fixed.
I still have a few plug-ins that were installed some time ago, they broke somewhere along the line, and are still not working.
I don't have unlimited funds, and there are other things I want to do with my site. If I constantly spend money to fix plug-ins, I won't have money to do the other things that I consider more important at this time.
Is there any reason I can't ride 3.0 out for a while and stick with my current version (I think it's 2.9.2)?