Roughly 1,100 miles (from a quick google maps hack), that's easily done if you're in good shape. As far as daylight, most people end up riding only 5-6 hours per day; if you can get out of bed and get rolling at a decent hour, you shouldn't have any problems there.
I'd advise having enough cash in reserve to hole up for two nights in a motel. End of October and beginning of November is when the first snowfall often hits the southern Appalachians. (For goodness' sake, learn how the natives say it before you hit the mountains. It is NOT pronounced like appellation south of the Mason-Dixon line!!)
Check out weatherspark.com for seasonal averages at some of the towns near where you'll be passing. I'd expect temps down to around freezing in the Appalachians in late October overnight, with highs in the 50s and 60s. That's a bit troublesome to ride in for me -- tights and jacket on, long gloves, jacket off, short gloves, jacket back on for a long downhill, jacket and tights off for the climb on the other side of the valley, lather, rinse, and repeat.
I think it sounds like a great trip. If you leave early enough, you might hit some great color in the mountains if the leaves are at their peak!