If I'm traveling with the BSR and tight on space (normally the case), I insist we both use Microfiber type materials for underwear and shirts. You can wash them out in the motel sink at night, and they'll be dry the next AM, if it's the right kind of materials. Same with socks. Most backpacking/skiing clothes work well for base layers. I wear long sleeved T's, even in summer...you stay cooler if they are the right kind of materials. I'm over buying HD T-shirts, unles I see something really different. Two pairs of jeans...one for riding, and one for not. If the ones for riding get funky, they just do. On trips longer than 5 days or so, I'll find a wash and fold laundry, leave the clothes, go eat, pick 'em up...or spend a couple of hours doing it myself.
I carry very basic tools...the kit HD furnished with the bike with some additions like zip ties, electrical tape, particualar hex wrenches not included in the kit, a shortened 1/2" open end for exhaust flange nuts (just in case), some spare tubing for my Legend Shock system, a small LED flashlight. Rarely carry spare oil, as it's too easy to find on the road, if needed (knocking on wood). Stop & Go tire plugger and CO2 cartridges with applicator. All my running lights are LED's or HID now. Oh, and a Gerber Multipurpose (small version) Tool, and I've got a genuine Swiss Army Knife (camping version) stuck in my lower glove box. If I can't fix it with that stuff, it's really broken, and time to call in help.
I try and select clothing, jackets, etc that are multifunctional and easy to care for...usually high end stuff, but it lasts forever. I just shop on line for sales.