I would not pay Disney premium like that when you’re spending only 2 days in the parks and doing other stuff in the area. I would also not put 5 people and all their luggage in a room that small.
These kids have never done a theme park but they are gonna cover everything they want to do in MK, EP & DHS in 2 days? Sure it’s possible (theoretically but DHS has a serious ride break down issue with ROTR at the center of that issue) but that might be asking a lot of those kids, those parks cover a lot of space. Maybe you or the parents have been to the parks and understand how much walking and standing that will involve? Because obviously then you know what they’re facing. (I just caution because people who have never been before tend to drastically underestimate the size of these parks and how physically taxing standing in lines is.)
If you’re gonna do it make sure you understand the outfit’s cancellation policy, some dvc rentals have nasty cancellation policies, many are non refundable so it may necessitate buying a travel insurance policy that covers the cost of the timeshare rental.
OP plans down days in between the park days. but we do marathon days all the time! And we do them back to back, not with down days in between.
I want to know what/how the group plans to eat, and what they will do during all that off-time.
What are the food plans? If OP plans to buy groceries and cook, then the condo makes sense. If they plan to eat out, then onsite makes sense.
For us, we're not fans of condos. We split our time between onsite and offsite hotels, and it is nice to have a room with a microwave/small fridge. We don't cook except coffee and maybe reheating leftovers. We do eat breakfast in the room, but IMO, cooking takes too much time. With what WDW costs, I want to make the most of every minute, but that's me.
Every choice has a trade-ff. Onsite and eating onsite costs much more, but you get to the parks faster and get more park time. Offsite/condo is more relaxed pace, but then it is harder to actually get to the parks. It is hard to stay offsite in a condo, cook, and make rope drop. Just there will tend to be a trade-off. You will save $ on food/hotel, but it is less immersive. Neither is wrong, just more/less right for you.
How well does everyone know each other? Five people in a Disney studio is not much privacy. I would happily do it with some people, but not with others. It really helps if everyone -more or less- goes to bed/wakes up at the same time. A condo = more privacy. The Boardwalk also has an awesome pool! The theming of the whole hotel is really fun and exciting, but it comes with a price.
Part of offsite stays and just one car is everyone has to come/go together. If you are at the Boardwalk, and the group wants to split up for a few hours, everyone can easily get back to the hotel. So again, it depends how you plan to structure your time.
It mostly boils down to how much everyone is on the same page. Personally, there is much to see right on WDW property. You could easily spend the whole time there, and still not see/do everything. I would perhaps consider limiting your group to one day trip.
