Difficult one because on the one hand it would be wrong to offend those who devote their time to maintaining this site but on the other hand it can't really be denied that this site looks and feels pretty dated.
The community here is one of the best on any programming-related site I have come across yet but when it comes to the UI I think nobody can say that this is intuitive. I have been around a while but I still don't quite know exaclty how to do all the marvellous things that are apparently possible on the site.
If you compare PM to a more recent site like stackoverflow.com then I think it is difficult to argue that PM is more useable. Better community - yes, more useful - yes, but in terms of useability, it's not that great.
Again, no offence meant to those who maintain this but it seems that there are people around who would be willing to contribute to an overhaul, so why not use that potential?

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