I rode with a bike trailer this summer in rolling terrain, and had to be meticulous with my shifting, because the extra load would cause me to slow down very fast if I didn't shift in time. The others were riding with panniers and I'd lose them in no time uphill if I didn't keep all the momentum I could. Ditto I wanted to keep up momentum going downhill.
This was on my mtb with a triple, but might be useful for you. I usually just shift by feel. Now I noticed that when I hit say a flat with uphills approaching after a downhill (highest gear) and started to slow down I'd downshift in the rear first, for several clicks. When I could feel that to maintain my cadence I'd have to downshift more, I'd downshift in front once to the middle and simultaneously upshift in the rear a click or two. This gave me a gear ratio very close to the one I already had, but in a position to downshift gradually. The middle chain ring is very forgiving for finetuning so I used that a lot since I couldn't stand and power through anything with the trailer on.
Give the simultaneous downshift/upshift a try and see if it helps to keep you in a range that's useful.
ETA: I see Oak said the exact same thing, only shorter and sweeter :-) No gears should be "hard" to shift into, in my opinion.
Last edited by lph; 08-21-2010 at 12:23 AM.
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett