Need driving/activity advice LA and W. Hollywood

[valiamo]

So, heading to Disney the end of the month. The boys (grown adults) have decided that they want to hit 2 concerts, so I have rented a vehicle. So we are driving up, dropping the kids off and then will have to find something to do for a couple of hours.

Questions galore....

- Concert 1 is at the Orpheum (on Broadway in LA) at 8:00 PM what time should we be leaving the Disney area, and is the I5 the best idea to head north on?

I figure if I leave around 5:30, we should be downtown my 7 or 7:30, sound reasonable?

Are there any activities that we can do while we wait (sights we should see, etc) keeping in mind it will be a Wednesday night?

- Concert 2 is at the House of Blues in W. Hollywood.

I see that we can take the I5, and then onto the 101 taking us into W. Hollywood. Again for a 8PM concert will leaving around the same time be reasonable?

Is Santa Monica too far away, or can we drop the kids off for their concert, and then drive west to Santa Monica for a couple of hours and then head back?

Driving back at around 11, how long do you think it will take to get back to Anaheim?

Thanks for any advice you could give.