You're very lucky to live where you do: Shenandoah NP and the Mt. Rogers/Grayson Highlands area are both lovely, and both are feasible long-weekend trips for you.

"...my thoughts to getting in shape and heading out into the woods." As long as you are aware of the risks, and don't push too hard too early, why not make it "getting in shape WHILE heading out into the woods"? Day hikes with a full pack, and lunch in the woods, help make the longer trips easier and more fun.

If you're looking to shave a few more pounds out of your pack, you've probably come to the right forum - just be prepared to possibly have your ego slightly bruised in the process! (We've all been there. Well, maybe not Jimshaw. ;))