This is a very valid point. I think they'll leave it as late as possible, as you never know what will happen, but I can really see that if they're looking likely to go down they'd do it this year rather than next. Right before the cut-off date.
Won't happen this season. No benefit for either Short or the loan company. This time next year if they have the same board then it would be nailed on.
Apart from the loan secured on the parachute money all the rest of the debt is to short. So why would he go into administration?
He's also got a few cast iron sales for players out on loan. They'll get some money for Kone, even if its £4m or so. Then there are assets like training and academy (i've already heard one is sold but never seen anything to confirm it) to be sold to property developers. All that, plus the second (3rd year less so) of parachute payments suggests Administration is at least a year away. Wishful thinking to say otherwise.
What would they do without the training ground? Get it back on rent?