I am looking into using some Aeroplan miles to book a bix class flight to Madrid. I see there are direct flight option to MAD from YYZ, but its on the older 767. There is also a connecting flight with AC to Munich on the 789, then a 5 hour wait to connect on Lufthansa from Munich to MAD.

What would be better, take the direct flight but on the older plane? or do the connecting through Munich on the newer 789? I am S100 with Air Canada, so the surcharges seems to be similar in both cases, and I don't mind too much doing a connecting if it means a more comfortable flight.

On another point, This would be a 3 weeks vacation with the wife and I, and the goal is to visit Madrid, then Barcelona and Lisbon. Should I fly home from Lisbon or Barcelona? I would buy separate airfare for the flights to Barcelona and Lisbon. Basically, what is better, from a logistics standpoint, Madrid, fly to Barcelona, then fly to Lisbon, then use Aeroplan miles to fly to YYZ from Lisbon. Or Madrid, fly to Lisbon, and fly to BCN, then use aeroplan to fly BCN to YYZ.
This trip will be in Dec/Jan, so just starting to get the planning down and nail those the business reward bookings on AC.
What would be a good distriubtion of days in those 3 areas? I was thinking 1 week in each area, with day trips.