I'd be nice to allow (and not produce error message) in case of several matches for log. For example, i have /var/log/nginx/ dir, where every nginx log is going. Some specific logs, which are used for statistics collection (machine parsable format, for example), can be rotated everyday, and kept for 1 day only. But if i produce two entires, like:

"/var/log/nginx/server.com.access.reqsize.log" {
      daily
..
}

and

/var/log/nginx/*.log {
        weekly
...}

i got the error on stderr (but exit code is 0) about duplication.
Most specific file match (pattern length which matched?) should win and do not produce errors.