I only wish that were true but these days I think people would rather just scream at CM's because of their own laziness and mismanagement of their vacation. That's why my wife loves me for my OCDness when it comes to planning our trips to the world.
--Mr. DB
Sometimes I book a trip less than a week out. I may not know if I can get time off until the last minute. So maybe the people wanting to go in June didn't know if they could go in June until a month or two ahead. That doesn't mean they are lazy or are purposefully mismanaging their trip. It may have been beyond their control. Of course, it also doesn't give the ones who are lazy and didn't do their research the right to take it out on the CM's and other guests. That's just plain rude!
But since you don't have to have a resort reservation to make ADR's, I'd suggest they try making the ADR's first and if they work out, then book the trip. I wouldn't pay the extra for the premium package without knowing for sure I could get TS three meals per day. They may decide on the regular package instead.
Another thing to think about, for people going during
free dining, is getting table service for lunch. I know a lot of people think they have to get the most expensive meals possible to "maximize" the plan, but last year during free dining, I did several walk ups for lunch, especially at resort restaurants, and then I found the CS restaurants to be much emptier at dinner. I wasn't on the
DDP, so it worked out better for me too. Lunch portions are usually a little smaller than dinner, for those people who have trouble with the quantity of food (I can never eat an appetizer AND entree AND dessert at the same meal).