I think the Classic in 100W, full power (vs. tweed) and diode rectifer will provide huge headroom. I don't think you can quite match this in the special which seems more geared toward getting that lower wattage bluesy sound like the old 15W Fender Champs or the newer Blues Junior.
Are you using a PA system? I'm playing with the LSS from small venues (100 persons) to indoor venues of 20,000 with no problems at all for stage volume with a PA. I dig the "Vox-esque" sound and the Mesa reliability!