I have been on the Oriskany three times, each time with different boats. For my money, call Chris Wachtel at 850-982-2995 and go with him on his boat, "Tech Rec.". This guy is all about making you comfortable and is very accommodating. His two daughters work with him and will haul your gear and set up your equipment between dives. His boat is well laid out for diving with ample space and a large covered area (important when you're offshore for that long). I cannot stress enough how much this guy works to make you comfortable. His boat is located at the Scuba Shack.
As for the actual dives on the "O", I have made 6 dives on her with aluminum 80's and have had no air issues. You can bounce the deck for a few minutes and then work your way back up and still have a good safety cushion for slow ascent and safety stop. Now of course I do closely monitor my air consumption. There is really not much to see at the flight deck but from 120 to 70 feet there is a a tremendous amount of area to dive. HINT: there is a lot of fishing line beginning to accumulate in some areas so be sure to bring a couple of cutters with you. Also, while the viz is usually pretty good, it has been less this summer than last year. Also, the temps seem to be a little cooler this year also. Another item you'll want is a good dive light.
It's best to divide the island into two parts and make each dive cover a different part so as to avoid overlap. Scuba Shack sells some excellent laminated charts of the wreck which will allow you to easliy plan your dive. Also, Chris has the same charts on his boat and can help you plan the best dive profile.
Enjoy!