why not start with the specs first? is a good practice on rails with all the power you have with rspec
Your Item should be called Post, why Item? is there any reason? if you want to call it "Item" you need to specify that on the associations
belongs_to :post, class_name: 'Item'
but you are better with Post instead of Item
A comment belongs to a user so the the user has_many :comments, you don't need the ", through: :posts" part
has_many :category_posts
has_many :posts, :through => :category_posts #or would has_and_belongs_to_many work better?
this depends on you, you need extra behavior on the CategoriesPosts? (Categories, in plural) if not, just use has_and_belongs_to_many
Really, i would suggest you start with the specs, you will end up with the implementations without thinking it too much and then you already have it tested and then you can add more specs and refactor it. Read something about TDD and BDD, it's hard at first but it's really good when you get it.