It wouldn't be a terrible deal for the OP to have to deal with this, as his friends are coming in same day. BUT, I can foreses many problems. We had looked at a vacation recently, but we were going to get two rooms at a value for the five of us with my Mom and step dad joining us for the last three days of the trip. (We'd then have 7 people total in two rooms, not an issue.) But, to get the dining plan (whether it's free or not) you have to get it for all in the party for the entire time. Since my parents weren't coming with for the beginning of the trip, we couldn't get two separate ressies with two separate dining plans and tickets. So, our plan had been to purchase the
DDP for the entire stay (and pay for it, mind you, no free dining at the time) and get the 7 day hoppers w/out expir. for everyone. Our plan actually included using some of "their" extra TS points toward a character breakfast one of the mornings they were there, and the rest of the extra over the time before they came.
With the "all checking in at one time" requirement with the free program, we'd be in trouble. What we were planning isn't all that unusual, and by Disney's insistance that everyone have the same dining plan and the same tickets, they kind of push us into getting more than what we need to get what we want.
I'd have thought that the ticket purchasing requirement would have eliminated most of the concerns about this? Seriously, how many people out there would purchase even the one day ticket to take advantage of the free dining for an extended period? One day ticket=63, that's almost two days of DDP. So, it would have to be someone paying for a one day ticket not only for the non-existant person, but also for themselves ('cause it's gotta be the same) and then they'd basically have to be staying for 3 days or longer to truly "take advantage" of the DDP,and even then, they would not have access to the parks on day 2-3. If a family was staying longer than 3 days, then it would be likely they'd be wanting tickets longer than just 1 day, and would be purchasing more tickets. If they are purchasing through disney, they'd have to purchase tickets for their non-existant person for the longer duration. If they are purchasing them outside of disney, they still will have paid disney $63 for each person they have on the trip, and to "break even" you have to be there for quite a few days. We priced it out once and it had to be something like 7 days or more when we added in the extra $63 for one day. The other scenarios that someone could truly take advantage, I suppose, is if someone had annual passes or leftover tickets, I suppose.
I guess what I'm saying is that it seems a bit of over-kill for Disney to respond so harshly to a situation that is possible, but really how probable?