We came back from a trip in June and have a trip planned for next May. This was our big debate also before we went and I am still not sure that we did the right thing. We were comparing 10 day no expire with the 5 plus options and park hopping vs dvc discount annual passes. We did buy annual passes for our family of 5, but we knew we were definately coming back within the year. Since then we also added a trip in August since our tickets are "free". So we will get 3 weeks on our annual passes. When we added the August week, then I really felt better about the annual pass purchase. Some things I like about the annual pass is the ability to just spend a morning or evening in the parks and not feel like you have wasted a day pass. Some things I didn't like about the pass is that I like to do other things at Disney vs going to the parks and with the annual pass, my husband was always lets go to the parks so we can take advantage of the annual pass. I also didn't think the Premium annual pass was worth it for our family of 5 (an extra $500 I think), and my 2 older children were bugging to go to TL which was vetoed by my husband as something to save for a time when we didn't have the annual passes. If we had the MYW, we would have received 5 opportunities to go to TL or any of the other places.
So I think if we would just have had 2 weeks on the annual pass, I would have considered it a very close toss up. With 3 weeks, I am a bit happier about the annual passes. I am not sure if we'll do it again, because 3 trips in one year is definately not the norm for us. But we will enjoy the rest of these annual passes.