I guess it all boils down to ... do you want to raid... with others.

if you do, schedule a few events and see who joins you. You have the advantage of being able to fill a few empty slots with your extra characters so in theory you should always be able to run an event. Per say some raid events are going to be extremely hard to multibox. What I hated most about raiding was people not showing up and having to PUG for extras. Raiding when everyone shows up on time is a blast, raiding when people quit showing up sucks.