Here's an update of my prep. I was feeling a little overwhelmed about all the things I wasn't sure that I need/want and space, weight, comfort, and cost. It helped a lot to do a practice pack of most everything I would bring. I didn't include food, but I'm keeping that to a minimum and some other small stuff that I made sure to have the room for.
I'm packing 4 days worth of clothes (i.e. socks, tee's and skivvies), plus what I wear, for 5 days total of clean clothes (with the exception of pants and shorts). I thought for organizational and ease of use that packing these in gallon size ziploc bags would be great. It'll help keep clean clothes separated from dirty, make organizing and access easy, and help reduce a little bit of space. I'm packing all my clothes in a backpack. I'll be able to do laundry when I arrive in the Seattle area (where I'll be staying for about 5-7 days) and again before I leave.
Backpack also has toiletries, utensils, maps and other small essentials. It'll go in the topcase, where I can also store my cook items, cool weather gloves and a few other small things.
One side case has sleeping bag and jacket liner. I may get a compression sack so I can get a little extra room in there.
The other side case has my camelbak and pillow (memory foam rolls up pretty nicely, I think I'll get a little stuff sack for it). I should probably put the camelbak on the bottom in case it leaks. A wet pillow would suck. Maybe a waterproof/resistant sack would be the way to go for the pillow.
Tent and sleeping pad on pillion. There's definitely room for a small camp chair.
What I have left to consider are:
Question for y'all, even if I'm camping in areas that don't get rain during the summer, is a dry bag of some kind still recommended?
Will likely get a kidney belt and airhawk2 cushion.
Feeling really good about how everything is coming along!
And Happy 4th to the US folks here!