I've done the ride North to South - so a couple of observations / suggestions.
* Depending on your cell provider, there are a fair amount of the Parkway where you'll have no service. Letting family know that in advance helps keep people calm.
* Asheville is a great town (with motorcycle parking!) Beer City USA. I've spent quite a bit of time there, PM me if you like.
* Fancy Gap Cabins and Campground https://fancygapcabinsandcampground.com/index.html
is *right* on the Parkway (a good day's ride from Asheville). I usually stay in the motel part (comfy bed, great shower) but staying there means riding up and down a decent gravel hill. I've done it on all of my bikes and never had an issue. Try the Hungry Farmer (about a ten minute ride, south on US52) for a ridiculously large meal.
* Mabry Mill for pancakes on the Parkway is a solid choice.
* There's no fuel on the Parkway, and the little map they give you at the information booths doesn't generally tell you which way (east or west) to go for fuel. Not sure how thirsty your bike is, but a gallon or so of fuel can be a comfort.
* Weather on the Parkway changes frequently, and quickly - I've experienced 40 degree swings in temperature in a day's ride. Not sure of your luggage setup, but keep the waterproofs near the top.
* Plenty of hotels in Waynesboro, NC (northern terminus of Parkway).
* From Waynesboro, Skyline Drive through Shenendoah is gorgeous. Speed limit is only 35, and while I've generally exceeded it, I hear a ticket would be pricey.
* Butler Maps (specifically the Southern/Mid-Atlantic maps) will get you good roads all the way to eastern PA. At that point, you really are going to have to hit highways. Approaching NYC from the south county roads are generally very residential, and state roads are full on highways.
* Usual caveats about toll plazas and oil and muck.
* Depending on your timing you are going to hit two separate rush hour crushes. Crossing the Hudson and crossing the East River. Neither are pleasant traffic-wise. I generally prefer the George Washington Bridge and then down either highway. West Side Highway means you have to cross Manhattan (I'm assuming your interest is quick, versus sightseeing). Harlem River Drive/FDR means the Cross Bronx Expressway.... HRD/FDR is like thunderdome. 40 MPH road with speeds of either 60+ or 15 and slower.
* Once you get settled in LIC, reach out. Always happy to show a new resident some of the best nearby roads.