Bummer! In my area (Indonesia) a large number of roads were added to the database using Digitalglobe / Maxar imagery. Now it is temporarily not possible to check if this date is correct, because Maxar usually has the most recent imagery available here in New Guinea. I hope this problem is resolved soon for JOSM

I also am concerned about suggesting highway=residential by default. While this is the most common type of road in towns and cities, in rural areas highway=unclassified is very common. Why not suggest highway=road? This is a generic tag and local mappers can improve it to a more specific value later.

Also, I’m curious how the tool performs in areas with lower-quality or poorer-resolution imagery. You must have found lots of this, here in Indonesia.

Do you consider imagery offsets?

This is also a good point. JOSM has an imagery offset database which can be quite helpful, but I don’t know if this is integrated into iD or RapiD. In areas like Indonesia, the default Bing imagery is often a few meters off of reality, though it is better than some imagery providers. You need to check local GPS traces to correct the offset.

Facebook … does not attribute OpenStreetMap in every map

This is a problem. I agree that facebook should properly attribute openstreetmap, and provide a link so that facebook users will know now to improve the map.

“When this inevitable moment of clash comes, I tend to care more about proper depicting WMAs than the outdoor.”

Your discussion here seems to be limited to a European context. There are many commercially available maps of European cities and the countryside and many free online maps for these areas, with different style preferences, so people have plenty of choices.

But in developing countries, such as in Africa and Asia, there may be no reliable map available besides OSM. And in 1 generation there are projected to be 6 billion people between these 2 continents alone. Shouldn’t the concerns of people in these areas have as much weight as making a nice-looking map for a European city centre?

(That said, I still want to thank you for all of the volunteer work you are doing for OSM, I really appreciate it!)