1) Consider a different mapping platform (preferably Google Maps). MapQuest is awful. Most of the time the map doesn't update, and when it does it has taken me over to Africa for no apparent reason.
2) I don't think Google Maps has a feature like this, but it would be nice to have "clustered" pins that expand as you zoom in. This way you don't have to try to get the perfect filter set before you can actually read the map.
I'm sure there are other things to consider adding, but this feature is basically broken at the moment. I had turned it on, but I'm going to have to turn it off until it actually works.