I haven't flown quite as much as Duck, but I've done my share of commuting to the airport. FWIW My experience with checked baggage is similar to his, problems I've had have been rare, and mostly resolved quickly. And, I agree, that the baggage fees are B.S. Southwest is your friend.
As for the flying with the gear issue, it probably won't be a big deal, but you should be prepared to answer questions, as long as they understand what they are looking at it shouldn't be an issue. I've flown with half my luggage (at least it seemed so) filled with disk drives, wall warts and power strips and it has sailed right through every time.
If feasible, I would treat the gear like a laptop and put it through separately from the luggage in separate bins, and allow a little extra time for getting through. It might not hurt to tell they guy checking ID's and boarding passes your situation and getting his advice too.
The security at Reagan seems pretty much always busy, so I don't think there is any possiblity of picking a slack time, but that would help too.
