Disney is always hiring but maybe not for what you want to do. Check the website and send in a resume.
The longest you can reserve a spot is 30 days. You can do back to back reservations if you want, but you're not guaranteed to get the same site for the 2nd reservation.
I would think the toughest part is to get a long enough, uninterrupted reservation, this is a very popular resort. As for hiring, probably just go to Disney website, human resources section and see if they have their open job postings, usually under some sort of careers tab.
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