If you bring a GPS device that you can download when you go out to do this skiing, that will go a long way toward creating a map. There's likely LIDAR data available to create a base, and combined with the GPS tracks, you'll be pretty close to being done, as far as ski-O quality is concerned.
I know. I have GPS'd my tracks 2 years ago. And I have done some Lidar downloading. Since it is rather flat I would have to add some vegetation, etc. which would not be too hard, I know the area so well. It's just all part of a long "to-do list".
Vegetation for ski-O? Open areas, I guess, but you can mostly see that stuff in aerial photos.