Consensus is it can be done then
I can’t see wanting to do it regularly, particularly if it’s difficult to keep the skirt on and water out of the cockpit, however it’s good to know that you can do it with a particular boat if something happens and the opportunity presents itself to get your boat upright without doing a wet exit. Still, if I can manage to do it without the skirt imploding and the boat filling with water that would be great. Even if the boat does fill with water, it’d still be better to be upright and able to bail rather than having to go through a self rescue with a boat full of water. Done that before and it’s a pain in the ass.
Don’t
know how wide it is but this one by Greenland paddler Adam Hanson is one of the most impressive rolls I’ve seen. http://www.youtube.com/user/oskaadventures
Ditto: Whitesell Piranha 34"
I don’t know how hard …
… rolling a SUP actually is, but notice that he submerges the end of it. That is also how some wide short stubby WW playboats roll so easy. My 27" or so play/river boat was just about impossible for me to roll initially (while I could pretty reliably roll the sea kayak) until I figured out how to use the slicing of the tail to my advantage. Now it feels just as easy and in “rough” conditions easier to roll than the same sea kayak…
Jay you missed people trying!
I’ll bring the straps and the beer it will be worth it to see another attempt! I guess you missed the Tarpon Challenge at the symposium.
Yes and no
In a true centered CtoC roll the seat back shouldn’t be a problem - theoretically. Most people tend to lean back when learning, and a layback is often considered easier to learn. So having that high back can make things a tad tougher.
But as above there are other reasons, which may not matter for you. Personally I find that a high seat back and a neo deck skirt are a poor combo for me - it makes the skirt tighten up behind in a very wrong place. But given the size of that cockpit, you may not want to go the bucks for a neo deck spray skirt, if one is available. So with your being taller and a nylon deck you may not notice that so much.
Looks like fun
Lokks like fun but certainly not practical. It would be easier to just climb back on. But I guess that’s not the point 
Gary