Please, Devon, do read www.cregox.com/your-home in case you haven't. That already answers most of your questions, and maybe a few you didn't have!
I have no clue on what you mean by "a mass drop style website" so links and screenshots showing references would be required.
Social features is a nice point in squarespace, they're really easy to add.
And calendar with options to vote on each item might be tricky, but it's sure doable. To have a better dimension on how you want this, again, please add links, screenshots or sketches of how you envision this.
After this, we may talk on skype if you want: caue.rego