The perspective mode of these maps could be a bit better handled. Such as, sometimes there are blocks of lots intruding in neighboring lots in odd ways. That's my complaint. Now, for the suggestion, make the perspective mode 3d-able. That is, you can turn the map any which way and will be able to see the backs of the buildings not shown while in perspective mode. To make sure it is done right, no below ground structures would be shown without the owner's permission (for towns & frontier). As far as frontier goes, there can be an exception made when "permanent" player made roads/railroads go through mountains or densely packed forest (in outer or nether worlds). I'm surprised that there isn't a dynamic map of The End. But I'm thinking that it's been suggested before for it to be added (maybe it is one of those back burner add on).
Dynmap is not managed by EMC. It is open-source, so EMC developers could work on it, but I don't think it should be a priority. If you want, you could check if your idea is in the feature requests here, but to be honest, I don't think this is going to be implemented, as it would probably be very hard to do (I haven't looked into the code and I've never programmed something like this, so I'm not certain, but I would be very surprised if this could be done in a reasonable timeframe).
