I'm going to be upgrading a blog from Wordpress 2.0.11 to the current version. Since 2.0.11 is the legacy version, will I run into any conflicts trying to upgrade? Thanks for any help!
You should not unless you have plugins which do not support the latest relase. To be on safe side, backup your whole site inlcuding files and database. You should also check the wordpress upgrade guide.
I've upgrade from 1.5.2 to 2.5.1 without problems - but as already mentioned, back up your db just in case.