This seems to be an obscure issue but I just tested and confirmed on SharePoint 2010 and wanted to see if anyone else had the same issue.
In SharePoint 2010, the first 16 people pickers are able to be filtered using [Me] but any pickers after 16 will not work.
I just tested by creating a list with 20 people picker columns, I populated them with myself. When using a view with a [Me] filter on PP1-16 it works fine, anything past 16 does not work.
Here is a link to an STP of the list I used to test.
https://dl.dropbox.com/u/70775/PPTest.stp
Old posts on the same issue:
http://social.msdn.microsoft.com/Forums/en-US/sharepointdevelopment/thread/634b3f24-b009-415d-8b45-40c11105b803
http://social.technet.microsoft.com/Forums/en-US/sharepointadminlegacy/thread/42874bd2-2f64-47f8-9393-c551b8242753/