Matt.....New York.......did a bit of car driving in Scotland a few years back. Came up past B'ham, dinner in Glasgow then B & Bs in Port William(? I think it was) and a nice one on Skye. Loved that place. Then over to Edinburgh for a day and a half and finally roll back down into England. I'm itching to get over there with a bike. Ride during the day and relax with a wee dram in the evenings. Your experiences lead me to think that an interesting approach would be to choose a good B & B or small hotel which is centrally located to a network of good day rides. Then use the lodgings as a place to to roost at night, reducing the need to carry a heavy load of gear. Just tools, water, snack, and of course....rain gear.
Looking forward to your continued reports.