In chop, there is no substitute for waterline. shorter boats are gonna get tossed around more than longer boats. So, knowing that, don't worry about what other boats are doing- do what works for you. Em, I don't know the balance of your boat, but if the forecast is calling for anything higher than 10-12, I leave the dock with main reefed. I can always release the reef, and roll out more jenny on the furler if conditions are more benign than expected.
It sounds like your biggest concern was the comfort of crew on deck while getting sail up, and that is a very valid concern to have. Sometimes the answer is counterintuitive- when it is choppy, power up the motor while raising sail rather than pwering down- try to match boat speed to the chop.
Yes, I typically motor out of the narrowish Herring Bay, and then put the sails up once out in the Chesapeake. Many do this to get in the bigger water faster. I noticed on my return trip that a few boats yesterday were putting up sails in Herring Bay itself, and one even while still in the channel behind the jetty. This seems like the smarter choice now - to get the sails up and reefed while still in relatively protected water.*
With regards to boat length, my ego was soothed slightly on my return to the slip by noticing that every other boat headed out was at least 5 feet longer than me. Even the big boats were rolling around quite a bit.
I'm going to see if I can sum up the advice I've read here: (1) get the sails up to increase power moving through the waves to keep the boat steady, (2) use a preventer to avoid accidental jibes on downwind choppy courses, (3) trim your boat for the wind conditions (thanks Alex for tips here), (4) move faster when getting the sails up and down in chop to stabilize the boat (and try to do this in relatively protected water), and (5) the shorter your waterline, the bouncier you will be in the chop, so take that into consideration in your plans (i.e. this will not be a pleasant afternoon picnic-and-beer-on-the-water day sail).
One final question with regard to crew sailing comfort - I experimented with multiple ways of heading into the waves and found that hitting them at an angle to my bow was more stable and comfortable than hitting them head on (lots of bucking up and down) or on the beam (rocking the boat back and forth like an out-of-control rocking chair). Having them at my stern at an angle was most comfortable of all. Does this accord with other's experience?
Did I sum this up correctly? Thanks for all the suggestions,
*Yesterday I had hoped that the Bay may be smoother, not choppier, in deeper water. It might be needless to point out at this stage that this is my first few months of sailing in the Bay, and I've been sailing Flying Scots in rivers until now. So this was my first experience with heavier chop.