Dh and I just returned from a 2 week, 2000 mile driving trip in Oregon. We each had a 21" roller bag and a backpack.
1. Dh just packed a rolling carry on bag (a 21" Travelpro)! I am slowly trying to get him to pack lighter and he originally said he would use a 24" roller but was able to pack less. We found a laundromat about a block from a B&B we were staying at, so did laundry halfway through.
2. I used my new eBags Piazza RFID Crossbody (https://www.ebags.com/product/ebags/villa-crossbody-20-wrfid/340525?productid=10688993) When you click on the link it says $49.99 I did not pay that. With the coupon code it was $20. It is a little bigger than I typically carry, but I ended up really liking it. I kept my phone in the open pocket, cash in the zippered pocket inside, receipts in one outside zippered pocket and my masks in the larger zipper pocked. I didn't worry about securing zippers, but it would be easy to do so.
3. We packed a small styrofoam cooler and carried a small roll of bubble wrap, along with a wine bag that was insulated and padded (for 6 bottles). We ended up buying vodka at Glacier 45 Distillery as well as wine at a variety of wineries and filled both. Even though there were some quite hot days, they stayed cool in the trunk and didn't roll around.
4. I packed a small soft sided cooler for water and a small plastic container with nuts and granola bars and the like. They stayed neatly on the floor in the back seat and were very useful, especially on a couple of our longer drive days and when there wasn't much on the road. I packed a large portable charger (https://www.amazon.com/gp/product/B01JIWQPMW/ref=ppx_yo_dt_b_asin_title_o03_s00?ie=UTF8&psc=1) and I was glad I did. We stayed in really older hotels and B&B's and plugs weren't always easily accessible. I often charged my phone with it on the nightstand. It is heavy and when I travel, I also have a 20000mAh bank I use instead. The battery on my phone is really poor and this helps a lot
1. I overpacked, yet again. Despite everything fitting easily in the roller bag, I still packed way too many tops. I also packed some things for work in my backpack, optimistically thinking I'd do it on our drives. Nope, I didn't. I still would have brought the backpack, but could have had less in it.
2. While I have decanted my toiletries, I could even go smaller. I had more than I needed for two weeks. I plan to rethink how much I carry. I thought I had it figured out, but need to look at it again.
3. I also discovered one of my small cosmetic jars didn't work well. Luckily dh could open it, but I couldn't. Basically the cream got on the side rivets (not sure that's the right word) when It was upside down and on its side. No matter how loose I closed it, it became tight and stuck. If you decant, try placing the container on its side and upside down and make sure this doesn't happen to you!
Oregon was beautiful and in our attempt to stay in very rural areas, we visited places we had never been before and probably would have never gone in normal circumstances.