I am a great advocate of Time Atac pedals, which you mentioned in your OP. The trap-style pedals all are pretty good, I think, because they don't rely on any mechanical mechanism to operate -- just springs.
If you have heelstrike issues, rather than getting a BoB, think about putting a front rack on the bike and carrying your stuff up there in panniers. It disposes of the heel-strike issue and may actually improve the handling and feel of your bike. The Volpe would have eyelets at the axle?
From what I am reading in your OP, your first venture will be an overnighter? A BoB would be overkill, unless you want to invest in one for many miles of touring later on (hopefully). But then BoB has a habit of encouraging people to overpack gear with stuff they may never use on a tour.
As to fitness, discuss here, too. If you're commuting, and you are setting out on an overnighter, you likely won't need to do much training at all. But the trip will certainly give you a feel for consecutive days of longer-distance riding than commuting. Many people, myself included, have started big trips with only a commuting base to work with, and have "ridden themselves" into fitness along the way by gradually building up their daily distances.
Rest is also important.