If you mean currently...

Lets say I head from high tower through the shadow grove all the way to the battlefields and back by way of the mountains south of galadon cutting through the weald in order to maximize the amount of time im in the wilds.

Assuming I do this fairly quickly and use the exact same path going in both directions then quaff to my hometown at the end of the circuit, a tracking ranger would have no means to know using track as it is currently is to know how long its been since I have been there, which direction I went in last, etc. they'd be on a closed loop trying to track me.

This is how I believe it works from an admittadly bad memory.

What track is good at is knowing someone has been here. That with a little bit of luck can help you find people. But to me thats just not what tracking is all about. Tracking is information gathering. And the way the skill works doesnt actually provide much information.