you would finally get roll back at 10.55pm and engine (1) started, which I understand allows a takeoff after 11.00pm but still pings the company the fine.
No. If departing off runway 16R the ground controller must utter the magic words "Clear to taxi" before 11:00pm; no fine even if you are airborne after 11:00.
On runway 34L you must be
airborne by 10:45pm to avoid the fine.
Certain scheduled flights may land between 5:00am and 6:00am but only on 34L. If conditions dictate 16 is required then you'll have to wait until 6:00am.
Ridiculously, you're perfectly approved to make as noisy a go-round as you like just after 11:00 or just before 5:00/6:00, but don't dare land and trundle through with idle reverse even seconds after or before these times!