What would be a proper way to simulate a large number of requests to test if my web application can handle it?
You could try using Microsoft's WCAT tools. Look here: http://support.microsoft.com/kb/231282
They're free, too. That's always nice.
Depending on your budget, you may be interested in some load testing software designed for this. A Google search brings up all sorts of alternatives. This is probably the best way to do it.
This one has a free trial version and isn't too pricey, but I would recommend shopping around first.
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