I have done this 3 times in the last 2 years of
free dining:
1. I always arrive with the kids at least 2-4 days ahead of my DH. He can only get a limited time off work so we go for 10 days and he joins us for 6-7.
2. The last 3 times we have arrived the last day of the freee dining window and all 3 times we have gotten it for lenght of stay. We just did it Dec. 16-25, 2011. We arrived on 12-16 (last day for FD) and got it for the entire trip.
3. Never once in a donze trip have they ever asked me for ID for my DH (which is good because he is never there). I check in, get all the passes and we are good.
4. The only down side is we often have unused days on my DH park tickets because everyone in the room has to be onthe same packege. However, the cost savings for FD far outways teh cost of the extra park tickets.
Have a great trip.