I always travel with extended family, usually with a smaller group (8 - 10), sometimes with a larger one (19). Sometimes we stay in one resort, sometimes two, sometimes each family picks their own resort and we meet up in the parks.
Personally, with the huge group, it was easier (and necessary) having our own space in our own resorts. With smaller groups, we were fine staying at one place or two (sometimes in connecting rooms, sometimes not)...we just text and meet up when we can.
Best advice, whether you stay in one resort or different ones, set expectations ahead of time.
What my family does is make a schedule...we plan ahead of time which parks we'll visit on each day, and then the night before that park visit will basically say, "We plan to leave for the park at this time. If you want to leave later, fine, just text us when you're leaving the resort so we can plan to meet up with you." The bulk of us usually leave on time (or meet up at the scheduled time if at different resorts), while those who sleep in meet up later via text. Even the late sleepers make sure to stick to our ADR times as we all like our food, lol. So far, it's worked fine for us.