Well lady luck is on my side. Managed to book flights from YYZ-ORD-ADD-BKK (stop) BKK-SIN-PER (stop) on 1 ticket (well 2 tickets with Mrs. Oldguy) for 220K points +$280tax for everything, J class the whole way, Absolutely brilliant and nice Aeroplan person, Ray, on the line who helped me tons.
Thanks to all who gave input and suggestions.
Reminder to self, start way earlier for 30th wedding anniversary.
Cheers all,
TOG66