^ Thanks for the feedback guys. Much appreciated and I am glad I am able to ask this question in advance on a discussion forum where ATC folks use on their available time from their work to answer with honesty and realism. I rather have this be discussed and tossed around here than at the airport when I try to bring that request to ATC prior to my flight when you guys are already in a high workload environment.
I am also aware of the lone R44 that does the progress shots of the airport hired thru the YYCAA but I am not likely allowed to tag along on that ride. I suppose the challenges of allowing this is still too risky at this time, I might just forget about it then. Maybe once new rwy ops is in full effect and the X-Wind rwys are seldom used I make the request for a photo orbit. I realize this kind of request has never been attempted before otherwise there would already be pictures of air to air yyc action.
There is one silver lining I have discovered, LR Helicopters will be in attendance for Wings and Wheels this weekend and will be doing sight seeing flights over the city. Part of their routing involves an overflight of the new runway possibly to offer a view of all the static items before turning south to do their loop. I may just tag along for one of those rides and request an deviation of the plan to do a teardrop loop over the new runway up to Juilet/midfield and return back to base thus covering photo ops of the static from the east and west ends.
Altitude would be whatever taxiing/approach height under pilot discretion. Probably similar to how Stars and HAWC maneuver around the airfield. Even a static coverage would be fine.
For the 787 departure, yes just PM me the punch codes to get into the old tower and I can gladly make my way up to the cab for some stellar views. I'll even dedicate my best shots to Nav Canada!

This weekend will certainly be a high exposure event for yyc and I just want to see if I can help show this through my photos. Plug a few shots on this board, airliners and jetphotos.net and see the rest of the world take notice. Not to mention Wings and Wheels will happen at the Air Museum for those who are into warbirds.