Thank you so much for the feedback. The hill challenge is still something we need to be prepared for. We live in Pennsylvania which is fairly hilly with some steep grades but not typically not more then one-mile. Extended climbing will be a new challenge for us. We've been following tandem teams who are using the Nomad trailers with good success. This summer, one of the folks on our Tandem Facebook group did the majority this ride, riding down to Santa Barbara, with three tandems all pulling the Nomad. So I think it will work OK, but I would love to know if anyone has used the Cargo Burley trailer which looks to be the same foot print but not enclosed. The Cargo is $100 cheaper and if you add back in the Burley Dry Bag which is 75 liters and $90 it's a bit cheaper. I'm guessing you can get a very nice large Dry Bag even cheaper then that. Using the Dry Bag would eliminate some of the issues of leaking with the Nomad. Thanks again and I'd love to know if anyone has used the Cargo trailer rather then the Nomad?