well this is a post with a very large scope to it. it is a lot easier to answer very specific questions 1 at a time.
i think an orderitems table is a good idea.
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how do i just pick out the items that have had a tick box ticked
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we need to see the html code you use to generate the tick box.
i'm a bit confused because up at the top you say you already have a site that takes product, quantity, and size... yet you're asking how to do it? are you adding more functionality to it? probably need to be more specific.