How long of a trip? Days? Miles per day?

I've ridden many miles with a rack on the back of my old Colnago Super road bike, including a few loaded touring rides (few days, usually). It is a little flexy which is a bit disconcerting, but it does ride well.

However, your Specialized Secteur is designed with flex, and I presume no rack mounts. Perhaps a seatpost rack, but I wouldn't load it down with racks.

So.. the trailer. I haven't towed a BOB around much, although I do quite a bit of towing a standard 2-wheel trailer around town. 50 mile or so a day isn't bad, but I dislike towing the trailer 100+ miles a day.

I recently took an 18 year old steel, rigid fork Jamis Hybrid, did some "road upgrades" to it and added drop bars. The conversion wasn't entirely cheap, although could have been down a little cheaper. Nonetheless, it has been a great utility bike for around town, and I no longer have the flex issues I felt with the old Colnago. I've only used rear racks in the past, but I'd like to add a front rack to the Jamis, and think it should work as a great medium duty touring bike.

Anyway, if it was me, I'd very much consider a touring/utility bike, but would consider used bikes, as well as building my own to my own specs.