One thing that might work, just for a trial basis, might be to partner everyone up?

Most of us know who is friends with who, so we could easily avoid the "usual" twosomes, and we could just see about making new CR with the characters that those two people have for that month.

Then! Once we are familiar with this person's characters we could recommend someone else in the game for them to get CR with. Maybe create some sort of CR phone tree of sorts?

It made more sense in my head... than when I tried to write it out.