I'm about to leave for our trip to WDW tomorrow morning. I cancelled a CRT breakfast for Weds at 8:10 for 2 by the way, but I couldn't find the CRT board to let anyone know!! Sorry!
It's very important that you do explain, communicate your expectations. This is your family vacation to WDW. You need to decide the date that's best for your family. How commited are they? We've gone two Augusts (last two weeks) for the past 2 years. The first year was cut short by Hurricane Frances, and the second year was perfect at the Beach Club Villas.
We've gone with friends on two occassions. One family was very Disney oriented. We just planned to meet for some meals mainly, and our kids didn't spend very much time with them, eventhough, we stayed at the same hotel. It was just weird, but now they're going through a divorce.
The other family was enthusiastic, but very WDW green. They didn't stick to the plan at all! Didn't book at the same resort, eventhough, they had plently of time to do so etc... ended up staying at the AKL without a car rental. I made the mistake of booking too many ADRs in full parties (should have split reservations) and had to wait up to 40 minutes for them to arrive! Needless to say, we learned very quickly to stick to our plan, and not wait for them.
My little one was disappointed that her friend didn't show up to the parks until 3 hours after she had! It wasn't fun!
This next trip, my son's friend's parents are bringing him to WDW because my son didn't want to go on a trip with them. I'm not sure how this one is going to turn out, but they expect my son to go off sight and play paint-ball all day. My son would normally want to, but he's there for the parks, water parks, disney quest, golf with Dad etc...plus, he mainly, wants to just "chill". I don't blame him. We've been to WDW so many times, that we plan, but don't over plan. It's truly like a second home to us. We rent cars and go into Orlando to shop/dine. At least, my son's friends parents knew to purchase the right type of ticket for him. My son will be going to every park, and back and forth to Epcot, Disney Quest etc...
You need to be upfront with how you and your family vacation. You shouldn't be confined by their morality, or their "tight" budget. Just be yourself and do what you want to do. Your family has taken the time to get to know WDW...purchased into the
DVC...your friends have the opportunity to do the same. That's my perspective. I'm not obligated to make mega-plans for people who don't bother to do it for themselves. I made it clear to this family that we're on vacation. I'm not taking their son around to tour the parks, and my son needs some alone time with us and his little sis. I just planned a couple of dinners at places that don't require a park entry (in consideration)--split ressies. I'll let them know which parks we are headed to on whichever days etc...I told them about adrs, tennis ressies (they like to play), spa, boat rentals etc...told them about this website, booked them a room at the OKW for 6/7 nights of their stay. They paid me for my points through Paypal. $10 per point...I showed them which ticket to buy for their son, so that he wouldn't be left out of anything. I told them to ask me any questions...gave them our flight numbers etc...
Hopefully, you'll take care of your family and your vacation time first. Make a list of what they want to do first, and plan it! It's fun with another family, but you just can't do "everything" with them. Stay at the same resort!