Nice post!
I too value the importance of exposing our children to the world by taking them overseas every 2-3 years since they were little, including an upcoming 3 weeks trip with our teenage boys to Italy this summer.
Flights - Aeroplan. Both my husband & I are SPG (CC) & Aeroplan (flights) collectors for years. We usually transfer enough points from SPG to AP for flight redemptions. We have just redeemed 4 open jaw tix to Italy this July from AP; I booked 2 tix each from our accounts on line followed by a call to the phone center to have the seats put together.
Hotel - SPG, especially if Cash & Points are available. Otherwise, it gets costly to book 2 room for the 4 of us. Even though European hotels room are not usually family-friendly, I find some local hotels are quite accommodating when you inquire with them directly. I was able to find hotel in Rome where the hotel will add an extra bed to a triple room to fit all of us, with an extra cost of 10 eruo! Deal!
It does take a lot of planning, points & $$. It is well worth it as we still laugh about some crazy things that we experience during our travel.
Do it, what their ages are, it's worth it!
As the boys are getting older & busy with their own life, I only wish we had done more adventures with them!