So I believe it will be difficult to get a ride to the start of segment two because it is out of the way, but you may get lucky. However, if you are starting seg2 simply because of the waterton canyon closure, then consider starting from the alternate trailhead located a mile south of waterton canyon. It is the same length and bypasses the construction work rejoining seg1. If you would like email me and i can send a kmz file for google earth showing the alternate trail
If you look at some of the other postings, you’ll find Trail Guy (and the email button). He is very helpful and I believe will offer you a ride from the Littleton transit station to the alternate TH. In fact the alternate TH is in his backyard!
To get to Littleton, take the airport bus to the downtown transit station then the train south to Littleton
Andrew M