WhitneyFan,
I am fascinated by your story. I too have done very very little backpacking mostly because of family obligations, logistics and time. So that has left me with long day hikes such as a 22 mile hike from Tenaya Lake to Clouds Rest to Half Dome to Yosemite Valley last summer where my family dropped me off and I met them in the Valley. This summer a big day hike of Crows Pass here in Alaska that covered about 24 miles and included a major league glacier river crossing. A bear also killed a moose on the trail the day after my hike which closed the trail for a few weeks. Anyway, if a person is in shape, they are manageable and quite enjoyable. I love the concept of a rim to rim dayhike.