Definitely will add a "good luck" to finding 3 seats available on all legs. On the exact days you want to fly.

Unless you're booking way out into the future or at the very last minute I doubt you will see that happen very frequently.

Your best bet is to split your group up, fly 2 and 1 if you want all J, otherwise deal with Y.

For me traveling by myself and a 100% flexible schedule, it is still not easy to find good flights booking six months out. I have to do things like drop my origin (small city, Aeroplan availability is never set up so I can make a connection in Toronto).

When I book for my parents, adding the second ticket drops available flights by at least 50%, and this is booking 9-11 months ahead.