The problem with playlists is that most missions are for 4 max - so as soon as we have more than that (or more than 6) we just end up doing races. It also makes it tough for people to join midway through.
I agree about the money - I have a fair bit but am just blowing cash in free roam at the moment
And am sure you have seen from my performance in the races that I don't usually earn too much from them!
I think it would work best to get everyone in our own session (like we do) but then do a mix of missions and races. There's no reason why we should only do jobs that enable everyone to join - no harm in doing a mission with 4 people, then a different group doing the next mission etc.
A few weeks ago there was pretty much 4 people on each night - so was easier to do a mix. Now that we are having 8+, then it makes it a bit more complicated to have variety.