It seems like you should detect whether there's already a map of a given place in an itinerary or on a day when doing an import of an updated flight plan.
1. upload a custom image for your trip and save it
2. click on Edit Trip Details
3. In the lower section of the page, the custom image is not shown, and no image is displayed:
Just because I have a 6 hour layover doesn't mean that I need a local map added to my itinerary. While this might be hard to detect, it seems like you could avoid this by looking at the time spent at a given location -- only if it's greater than 24 hours, maybe add the map?
Wouldn't it make more sense to offer an easier way to pick my timezone rather than a GMT dropdown picker? It's impossible to do type-ahead and just feels painful to try to figure it out...