My family's 1st trip to Disney World was in January, 2008 (I went twice in the 1970's and I remember staying off-site and a few rides but don't remember anything about dining!

). I was 20 weeks pregnant with child #3 and had a not quite 2 year old and not quite 4 year old. We had my mother-in-law with us as well as our au pair. I read the Unofficial Guide with Kids. Or I read part of it. We stayed at the Polynesian and had no ADRs. (I'm wrong. My DH and I had a reservation for Victoria and Albert's for a date night.) We still had a wonderful trip but we found it incredibly frustrating that we couldn't eat sit-down meals. Once we realized that we needed ADRs, we called the dining number and got an ADR for 'Ohana for later in the trip (the food wasn't very good - I've read that it's gotten better recently). We ate many meals at Kona Cafe since you didn't seem to need an ADR for that.
Our 2nd trip was May, 2009. We called for ADRs about 2 weeks before our trip. We were traveling with our 3 kids, my parents, my stepsister and her family (DH and 2 kids). We still hadn't really learned our lesson! We were staying at SSR and had many meals at Downtown Disney since that was the only place I could get ADRs at that point in time! We had learned about ADRs but not the part about 180 days in advance...

We generally like to eat sit-down meals but I absolutely HATE having to plan so far in advance. We probably change 1/2 of our dinners by the time the trip arrives because our plans change. I go to Disney to be on vacation, not to have a schedule that I have to follow with military-type precision! We're slowly moving away from so many sit-down meals, not because we don't like them, but because our family needs more flexibility. Kids get tired or hungry at the "wrong" time. Or we're having fun and don't want to stop because we have an ADR that we scheduled 6 months ago. I know that there is no good answer to this. Part of me wishes that Disney left about 30% of tables unreserved, although I realize this would create it's own set of problems.
As an aside we have NEVER gone during peak season. We go for Marathon Weekend (and we had to change 2/3 of our dinner reservations because my parents decided to join us 3 weeks before the trip and we couldn't add 2 extra people to our ADRs. Still had great meals!). We also go the last week of August which is generally pretty empty since most schools outside the Northeast are back in session.
One more thought... As the local Disney expert I get a lot of emails from other parents who are going to Disney World. One friend emailed me about 2 weeks before their Christmas break trip. She had NO ADRs and didn't realize they would need them!

She was very grateful for my help but more than a bit annoyed that she couldn't get into many of the character meals (she has a 3 year old and a 5 year old). So I don't think most non-DISer types understand about ADRs.
My 180 day window for our August trip opens soon and I'm honestly not sure what I will do. Many of the places we want to eat seem to not fill up terribly quickly (my 6 year old's favorite restaurant is Bluezoo!). Maybe I'll book Garden Grill and Teppan Edo and Cape May Cafe and then wait until the travel dates get closer to pick the rest?
Amanda