The 'ol K&N filter theory! Most or all filters filter better with clogging since the dirt prefilters out other dirt (a pretty funny concept when you think about it). But overall, dirt accumulation is not a beneficial thing, and filters are designed to filter well -- down to a given micron rating -- even when brand new. If a given auto manufacturer recommends filter changes every OTHER oil service, it's due to a desire to ease maintenance, rather than the idea that an "old" oil filter will perform better and is therefore desirable.
"How old can a filter be before the media would break down with age?" Nobody can answer that -- it all depends -- but I've read that one reason for newer synthetic oil filter medias is to counter media deterioration caused by acids accumulating over extended drains. That said, I'd never change a filter due to a concern that the media may be "breaking down." Not an issue in my opinion -- all oil filters are designed for 7,500+ mi extended service these days.