US 58's a fun drive. The climb up the Blue Ridge from Stuart is two lanes, but it's quite scenic. There's a four-lane bypass of Meadows of Dan (where the business route intersects the Blue Ridge Parkway) and more of the four-lane has been built east of Hillsville.
Once you're on I-77, would it be faster to stay on 77 all the way to the Ohio Turnpike, or would US 33 or US 35 be better options? Both cut the corner diagonally to whatever route you'd choose to head north on (possibly US 23 out of Columbus or I-75 out of Dayton.)
If you opt for the I-68 clinch, an alternative is to take US 522 out of Winchester, Va., to Hancock, Md. It's four lanes in Virginia, a super-2 for its short length in Maryland, and the West Virginia portion isn't that bad. How you'd get there from I-95 is something on which I could not give an expert opinion, although US 17/I-66/US 17/US 50 from Fredericksburg is an option.
With all the new construction that has been done over the years, the fastest option for me would involve making my way to Winston-Salem, then US 52, I-74, I-77, and I-81 to Abington, then following Alt. US 58 and US 23 into Kentucky. Because of high water road closures on what would have been our family's normal route to the Outer Banks back then -- and my dad's stubborn insistence that if he encountered high water, even if only about 90 minutes from home, we'd turn around and come back home and not take the trip -- we opted for the route through Hazard, Whitesburg, Norton, and Abingdon. We ended up exiting I-77 at Hillsville and using US 52 into North Carolina because the I-74 connection hadn't been built then, and maps didn't show any other exits between US 58 and the state line.