Thanks
I created a OsmAnd+ way point with the coords
The way point is right at the bridge in my screen shot
This is the waypoint text

Lake Logan Road, Burnett Siding
Location: geo:35.373367,-82.93769?z=16
https://osmand.net/go?lat=35.373367&lon=-82.93769&z=16

Clicking on the url above does not show grn mtn trail, but it show up in OsmAnd+ and in the editors

Fork ridge trail measurement is able to snap to the trail
You can save the gpx file and open it in my places as a route that follows the trail

Green Mountain trail is not doing this
Saving Grn Mtn as a .gpx and the going into my places, you get a straight line between the two points

It looks like OsmAnd+ is doing something after you create the 2nd point on Grn Mtn
But the route is not visible over the top of the trail like it is on Fork Ridge

Check out my screen shot
See how Fork ridge is a solid purple after measuring?

Grn Mountain does not show the route after measuring