well, I don't travel with a family, but I think in any case arranging an important dinner on an arrival date is possibly unwise - especially when traveling by air. Could still be arranged with no monetary penalty resulting from travel delays, should they occur. I'd caution strongly against making an ADR on an arrival date at any restaurant that requires prepayment in full or a credit card guarantee.
First, last, or in the middle doesn't matter to me. I go more by what day I plan to be in what park, but if I can't get an ADR for that day, I'll take whatever ADR I can get and hop or change our park schedule around it.
Our first meal is always the biggie. We usually do DTD or play around the resort(s) on arrival day and hit MK the next morning. We prefer to start the trip with a pre-opening ADR at CRT or CP. If we're more relaxed, any character breakfast (we did Cape May in December) is fun to start the week.
I usually get our ADRs in the first part of the trip, and we take a much slower pace toward the end, eating wherever we happen to end up or even heading off-site to grab a meal.
Last trip I saved DS's special meal (Jiko) for our last night and he ended up coming down with an awful stomach flu! I know that is something that cannot be predicted but this year I promised him Jiko on our first full (non-travel) day!
both...we always have a special dinner our first night there and a special dinner our last night there followed by "kids park choice" for the last park to visit before we leave. Thsi trip our first night we are doing hoop dee doo for the first dinner and last dinner we picked 1900 park fare character dinner. have fun !
forgot to mention we also do chef mickey's for breakfast our first full day there to kick it off with some "character" and we always begin our week with the MK in terms of parks we visit.
Our family makes the first meal the special one because the last is usually in a rush or at the airport. If we can, we try and make the last one be EOS and we take it with us and eat it at the airport. Perfect way to end a vacation
Our favorite restaurant is 'Ohana. We start and end our vacation with this restaurant. I book it for the first night and for the last! If I had to chose it for just one day it would have to be the first day. I couldn't go through my whole trip waiting to eat there.