My local REI has the Port Townsend and the Clubman in stock and I really like the looks of these bikes, but I was hoping to get some food for thought/insight/considerations on the Port Townsend before I go down there and start testing everything out. The few things I've found point to the Port Townsend as being very heavy and

I ride with a Carridice Camper (lunch+work clothes+cycling necessities) and water bottles and that's about it. My ride:
a.) LOTS of hills on the commute. If you aren't going down you are going up and there is pretty much no level ground (Mission Viejo, Ca area). The commute is about 8 miles each way.

b.) I haul my daughter in a trailer a few days a week although I may switch to a back seat style when I buy the new commuter.

c.) I want to do short tours on the bike. Four days self-sustained out and back max. Most will be 1-2 days.

*I know a lot of people point to the LHT...for everything, but I have yet to find a single store that has one in stock around me.