Book for a person who may not come?

[HooKooDooKu]

You can generally INCREASE a package; add guests, dining or improve tickets without a penalty. Did you ask if you could DROP a guest without paying a penalty. This could be an issue with free dining, if the resort required all guests be present, but would be a bigger issue with paid dining.

As long as you are still 45 days or more out, you can DECREASE your package without a penalty. The only exception would be if you completely cancelled your trip AND you purchased insurance. I believe the cost of the insurance will be deducted from your refund.

Once you are inside that 45 day mark, there is a penalty for making a change to your package that reduces the price. I think the penalty is $50. This goes for any WDW package, not just the free dining.

Otherwise, because the "free dining" is connected to the room reservation, and EVERYONE in the party MUST have the plan, you can make changes up or down until that 72 hour mark. So if someone is questionable on attending, its going to be better to NOT book them initially and add them at the ALMOST (72 hours) last minute. I haven't seen a down side to that plan yet.

The only thing you might have problems with is changing the number of days for your reservation. Each resort has a limited number of "free dining" plans available, and I have NOT been able to figure out how they calculate this. When I tried to initially make "free dining" reservations last week, several of the days I tried were already full, but I couldn't find an exact pattern. For example, at one point last week I wanted to book a Sat to Sat 7 night stay @ Pop. But Pop was already full for those dates. If I wanted to stay @ Pop, I had to either decrease the days (Sat to Fri for 6 nights) or increase the days (Sat to Mon for 9 nights) for the free dining to be available.

 

[clkelley]

If I wanted to stay @ Pop, I had to either decrease the days (Sat to Fri for 6 nights) or increase the days (Sat to Mon for 9 nights) for the free dining to be available.

Well then that's easy, book the 9 nites, pay the deposit, then call back later and drop the nights you don't want.

 

[kdzgon]

You can’t purchase a one-day base pass for the Guest who might come, while purchasing a different length/type/options for the rest of your party. Everyone on the package reservation has to have the same MYW pass. The only way to do this is to change the package to include one day base passes for everyone, then upgrade them while checking in.
In addition, you wouldn’t be out $30 if that person didn’t come, you’d be out about $70.

Pumbaa/other Moderators, if this post violates anything, PLEASE feel free to delete it. I think I’m just explaining rules, but I’ve been wrong before 

I'd look at it as not quite being "out" the $70, as you would still have that pass, wouldn't you? Or, will you then be charged the $50 change fee at check-in?

If you upgrade at check-in, do you pay the advance price, or gate price for the upgraded tix?

Will they allow you to trade in two unused 1-day base passes towards one multi-day hopper pass?