I guess you use the 4.6.6 version, not 4.5.5 as stated in your signature.
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1. How do I add the number of items in cart to display in the "Shopping Cart" tab (in addition to "cart")
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Do you mean the black "Shopping cart" tab at the top of the page? If so, it is the "Speed bar" -
http://help.x-cart.com/index.php?title=X-Cart:Speed_Bar
It is just a list of links that you can manage in the back end, and it doesn't show the number of items in the cart.
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2. How do I add a pop up window when customer adds an item to cart that would include the "continue shopping" and "Proceed to checkout" buttons?
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As far as I see the product page displays variants in a table. Is it a custom mod? It may that this is the thing that cause the "Add to cart Pop-up" stop working.