Our 3rd was scored in the 80th minute, not the 70th. The game ebbs and flows, just because you're on top for a spell doesn't mean you can maintain that for the remainder of the game, we had to compensate for the fact that Sheffield were going to come on strong.
It's not a matter of pressing, it's initial positioning, I think the players are encouraged to pack the box in that situation which not only invites pressure but infact requires greater effort to close down wide players when they invariably spot this and take all the time they need to play the best cross. It's the opposite of what you're saying. It's energy-conserving to maintain presence in wide areas there.
It doesn't seem rational to me that you could disregard Ole as a fundamentally flawed manager on that basis, he has to learn how to see out games for sure but that's not a basic understanding you'd automatically expect any manager to have otherwise very few goals would ever be conceded from winning positions late in the game, he has to be given the time to learn from his mistakes.