The satellite images used in the Create a Trail option are at least several years out of date. There are trails in my area that are difficult to draw or visualize because construction has been completed but the images are missing roads and connections. Example, trails along Wurzbach Parkway in north central San Antonio.
Thanks for reaching out! We actually rely on a third party (Mapbox) for our map tiles. This just means that we aren't able to update the satellite imagery on our site until Mapbox updates their data/imagery. It doesn't look like they have a set schedule for updates, but you can send them feedback on your area here
Hopefully, the satellite imagery for your area is updated sooner vs. later since it sounds like it has been a while!