Chris I'm not sure about your GPS model, it may not have "route capacity", but my Garmin II+ did have them and I would tell to follow say route 2 and it would take to each waypoint in succession and flash "approaching way point" then after reaching it, it would look for the next way point. Seems to me that if you didn't actually go close enough to each way point it didn't know to start looking for the next.

Now I use google Earth at home to locate the road or trail intersections and any funky spots to be careful of and load them in. I don't use routes on my foretrex, but whenever I get to an intersection I have notes saying which way to go, and of course backtracking is easy. Yes I print maps...

A hint is to not leave it on all of the time, just turn it on at critical points and ALWAYS TAKE THE TIME TO SET A WAYPOINT AT YOUR TRUCK IF YOU HIKE AWAY FROM IT. This saves batteries, always have a spare set of batteries.

However as an old camping buddy said - Jim yer an experienced engineer, operating the gear is second nature to you, not to everyone. I used to install military models with altitude, angle of attack and other flying parameters, in RPVs.
Jim