I've done this twice...both times I reserved 2 studios, one for me and one for my friends. Did both reservations at the same time (on the same call to MS)...started with "I need to book two studios, one for me and one for my friend and her family"...MS booked each studio separately (taking names, addresses, etc for each villa)...then I added DDP to one of the two reservations, but not to the other...Worked fine...no problems at all...
The reservations showed up as two separate reservations on the website--we never even discussed linking, altho I did ask that we be placed close to each other (I wound up in a studio directly upstairs from the one my friends had, at OKW (Turtle Pond)...it was great...(the other one hasn't happened yet...that trip comes in Feb)...
Hope this helps...