If you reach the lean-to, you’ve passed the herd path. There are some yellow paint marks on some trees and rocks to follow most of the way along the stretch between the state trail and Panther Brook.
Couchee is one of my favorites, also (officially, per my final Forty-Sixer report, my second-favorite of the High Peaks). If you think you’re making good time, you may want to head out there first, then see how you’re doing when you return to Times Square. It’s a long way out, so it will probably take you more time than you think. Then it will be another two hours to get out to Santanoni and back. Panther is less than 15 minutes each way, but I always seem to end up spending a half hour on top. It’s pretty steep getting up onto its summit plateau; the sign is back in the trees on the right. The trail can be mushy getting back there.
I’ve been up the herd path thrice, but never even attempted hitting all three peaks in one go. And the road walk out at the end is interminable.
Have fun!