We rarely purchase Early Bird. We set an alarm and check in exactly 24 hours from the flight. We're almost always low in the B group, which leaves plenty of seats together for the 4 of us to manage sitting 2 and 2. In the instance we feel the need to purchase Early Bird, we will typically only purchase for 2 of us, and leave the other 2 without. They are usually able to sit where there's a seat left beside them by the time the rest of us board. It's a bit of a gamble, but saves some $.
If you get the SW Visa and use it for your spending, you'll get automatic A-list. My DH never has to buy Early Bird anymore, but always has A seating. The rest of us don't (even when flying with him), but it's really not that big of a deal most of the time. So, for our upcoming trip, we may purchase Early Bird for one of our kids & send that kid on with him, then the other kid will go with me.