I've spent a ton of time mapping out trails in my region on openstreetmap. I've found the issue now is the interface. The map data is only good if it can be easily read.

I'm starting to look at workflows for taking osm trail data and trying to make nice maps, but wow it is not easy to do!

Thanks! I use mapy.cz for everything, but my main reason are the hiking routes. I've contibuted some routes also (and city data using streetComplete), but certainly not a ton.

Agreed. It has the potential to be best bar none for this. Where it isn't, it is probably only a matter of time.