About the packing issues....here's what I found last time around:

1. Cutting down on number of items: Very little is needed in terms of non-cycle clothing for on the ride. After the day's riding, I would shower, put on my pj's (alc flannel pants and t-shirt) and a sweatshirt (alc fleece bought in camp) for the evening and it was the same pj outfit for the whole week. So never used any "normal" clothes for the week. Also, the cycling-related clothes that take up more room are of course the larger items for cooler weather. I only brought one set and used it all week (long-sleeved jearsey and wind-breaker jacket and leg-warmers for those chilly mornings). That only leaves a few "normal" clothes for the days before/after the ride. And for that, I will be very spartan in my packing. There will be no outfits for "just in case I need to dress up" for instance or "just in case we find time for...". Which mainly means, I will not be bringing lots of different pairs of shoes. it will be cycling shoes and trainers, no hiking shoes just in case or dress shoes just in case. And I will plan on being able to do laundry during that week in Sonoma which cuts down on the number of changes of clothes needed.

2. Making room: I found it easier to fit the sleeping bag when it wasn't stuffed into the sleeping bag stuff sack. Instead, I used the mesh pocket in the lid of the suitcase and folded the sleeping bag flat in there. took a little stuffing and cursing, but worked. Seems counter-intuitive perhaps, but it made better uses of the space. A round stuffed sleeping bag, even well compressed in the compression sack just made for too many underutilized crevices and made it hard to pack everything else well.

3. When there is still not enough room: I didn't need to, but I did see some people had their sleeping bag and/or mattress pad strapped to the outside of their duffel bags (using strong baggage straps, not bungy cords of course).