I don't think I've ever booked directly with Worryfree Vacations, but I believe Northwest WorldVacations is pretty much the same operation, except that they don't offer the Champion Air charters. When I book with WorldVacations, it shows up on nwa.com in my record and I can choose seats based on status. That said, you may need to get the gate agent to do your upgrade. We flew back from the Bahamas Tuesday in row 5 looking at a half dozen empty FC seats deadheading back because I didn't do that. I didn't do OLCI because I didn't have a way to print the BPs and there are no kiosks to reprint them at the Nassau airport. It was a mistake on my part. Delta handles the check-in there.

The automatic upgrade SHOULD still carry, but didn't. Complicating matters was that these were award tickets. The upgrade still should have cleared 24 hours prior for this situation.