questionshow do you add different items to the same order…

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If you are talking about any of the Woot related costs, Woot does not have a shopping cart feature. Fortunately, they have a promotion going on where you pay the $5 standard shipping fee once and then all the rest of your orders qualify for free shipping on the same day. One thing to note is this does not cover the faster shipping methods or orders on separate days.

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Directly from the FAQ
http://www.woot.com/faq

What is this "$5 All You Can Ship" thing about?
OK, standard shipping for a Woot order is $5, right? Well, check this out: once you've paid that five bucks to ship an order from Woot, you get free standard shipping on anything else you buy from any Woot site that day (until midnight Central time). That's right: a fiver covers all your Woot shipping for the day, no matter how much you buy. So buy early and often to get the most out of that fun. For now, we're calling this an experiment, so take full advantage of it while you can.

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If you're talking about Amazon, http://www.filleritem.com/ is a great tool - just fill in how much more you need to qualify for free shipping, and it'll give you a list of things you can add to hit that $25 free shipping threshold. That said, Amazon Prime is pretty awesome too. :)