Question 2: What would an interaction between Captain Cold and Warden Wolfe look like (assuming both were being written roughly in the way that Geoff Johns depicted them)? Johns never had them interact, but I'm really curious what it would look like if he had.
It'd be one hell of a battle of wills, and Len wouldn't back down. Wolfe wouldn't either, and I'm afraid that he'd probably do a lot of damage to Len in the process -- likely killing him or coming close to it unless someone intervenes. I don't know whether a guard in Iron Heights would care enough to stop it, but somebody might. Most likely any intervention would come from McCulloch or possibly the Flash, if Wally happened to hear about it (maybe even from Evan tipping him off if he could see what was happening but unable to act himself).
It's possible that Wolfe would be satisfied with teaching Len some lessons and just moderately torturing him bit by bit over time, but I think he'd get really pissed by Len's defiance and things would get very bad even if Wolfe hadn't meant to go that far. He's a control freak and gets enraged by defiance or even people disagreeing with him, so I think it's for the best that they never met in the Johns era, as it'd get very ugly. It does however suggest a potential plotbunny of a major conflict between the Rogues and Wolfe + his loyalists..!