Later this year(in either october or november) I will fly on a Visit NA Airpass. First I only planed on flying 3 segments but now I am thinking about flying 5 segments and try to reach as much miles as possible.

One problem is that I can only make two direct flights between these cities

GROUP A
BDL/BOS/BWI/DCA/EWR/IAD/JFK
LGA/MIA/ORL/TPA/PHL/YYZ/YUL
YHZ/YOW

GROUP B
BUR/LAX/OAK/ONT/PDX/SAN/SEA
SFO/SJC/SMF/SNA/YVR/YYC/YEG
HNL

One flight will be JFK-YVR(One of my transcon flights). My 2nd leg will probably be YYJ-YYZ(YYJ is not listed above so this will NOT count as a transcon). I can fly both UA and AC but I would prefer AC since I can upgrade those flights. I would also prefer cities with NHL teams.

Would YYZ-LAX be a good 3rd segment? What about the last two? Any other "secret routes" as YYJ-YYZ?