I missed this topic until now, so I'm late to the party.
I MAY be starting a new job in January, so I may not even be able to go, but assuming I can go, here's my thoughts. If it were Boston, I like the idea of taking 448 to SPG on Sunday to meet the commuter line to New Haven and beyond. If we're talking about going 3 days, is it possible to do the Brunswick turn on Monday or Friday? But I see from reading that we've probably moved south. I'm willing to wait until 2020 for Boston.
I don't see much appeal to the Roanoke turn as a group. Just seems boring and the fact it would be dark for the ride down. When I'm with the group I really enjoy doing multiple rail rides and checking out different types of transit.
I definitely like the Florida idea. I'd probably just fly down there and skip the long distance rides, but I've been wanting to ride Brightline and some of the other rail options that Miami has to offer. It's been years since I've been.
As for NC, that'd be my second choice. RGH is a nice station and worth checking out. I drove by it a few weeks ago and stopped but I didn't get to the board the train as they don't let you on the platform unless you have a ticket. I'd probably ride the Crescent up or down too from NOL.
So my choices in order are:
#1: Florida
#2: North Carolina
#3 Roanoke