I can't join you but if you get a car spot, I'd do it as a day-hike. Last October I did much of the same trip. AT from Route 41, up Jug End to Race & then Race Brook. I would have done more but I was solo, spotted my car at Race Brook & rode my bike to the start. I didn't want to ride any longer so that's why I choose Race Brook. Had plenty of time
In a perfect world you'd have three cars. One for Undermountain & one for Salisbury below Lion's Head. Lion's Head would be the goal but if a car is at Undermountain & everyone is beat after Sage's Ravine, you can bail on Paradise Lane with very little elevation gain from the jct with the AT back to Undermountain. If only choice is below Lion's Head you've got a decent climb up to Bear & then it's still several miles over Lion's Head & down.