As i do more and more maps in a particular region DD UI gets clogged up and finding maps quickly, and correctly, i can see is going to be an issue continuously as the number will only go up. If we could create tags for flights that allowed us to quickly filter by the tag, and not just the name, it would make a very extensible approach to finding maps with particular features, locations, dates, etc. regardless of the quantities of maps being created.
Tags would be great. I can see some kind of folder system working well, too. Maybe an expandable / collapsible hierarchy tree.
A Google Earth type of folder system would be immensely helpful. The default sort by date is ok, but if you fly the same or nearby locations over time or for different reasons, those locations get spread out and disorganized.
Even a simple sort to get started would be extremely helpful. For example, a simple drag and drop map sorting GUI: