So my inquiry on doable connection time is for two diff dates 5 months apart (I'm booking these as RT JFK-YYZ to make use of a fixed award chart):

FWIW, Canadian Passport, have TSA Pre (Nexus)

Date 1:
May 22nd, 2023 (Long weekend for Canadians FWIW)
Inbound Flight FRA-JFK on SQ, arriving at 11:10am, no checked luggage
Outbound Flight JFK-YYZ on AC, leaving at 1:25pm, no checked luggage (or gate checked depending on how generous the gate agents are feeling)

Date 2:
Oct 19, 2023
Inbound Flight YYZ-JFK on AC, arriving at 10:06pm no checked luggage (or gate checked depending on how generous the gate agents are feeling)
Outbound Flight JFK-HKG on CX, leaving at 12:25am no checked luggage

Would these be feasible? I think Date 1 is very doable but Date 2 can seem concerning because I've been burned by AC delaying a flight extremely long time before (forcing me to miss ANA F...)
Otherwise I'll be routing through LGA (flying into LGA at around 6:41pm to account for ~1h commute to JFK [overkill, yes]).

TIA!