WordPress hands down might be the best blogging platform around, but with so many changes so quickly do you really need to upgrade today? I always say when it comes to upgrades on blogs or on standard Operating systems, unless the update is a critical patch don’t upgrade immediately. Most of the time you find that if you don’t need to upgrade then take your time and let the experts do all the break fix testing.
Give the community time to download and install especially those who are new to blogging and WordPress. I would say give it about a month before going for the upgrade and if there are plug-ins that you use check out the developers site to see if they have checked that it works or is having issues before you upgrade. WordPress is at version 2.8 which means in my opinion if your at anything below 2.7 you need to a least upgrade to 2.7. With that said please check your plug-ins before upgrading this will help you in the long run.
On the other hand WordPress 2.8 seems to be another great release from the guys/gals at wordpress.org. They say that over 700 fixes have been made to this version. WordPress has release a video that shows some of the improvements and I would say those improvements alone are reason to upgrade, but again wait a month and I think you well be out of hot water by then.