Sitefinity is a native ASP.NET 2 application which means that you will need to have Sitefinity files inside of an IIS application. Obviously, web.config will have to be the one that you will get from Sitefinity as well as you will need to have all the necessary binaries in the bin folder.
As for your second question, Sitefinity has built in url rewriting features for all the modules and pages. We also support multiple urls for pages. You can download a free demo and give it a spin.
Thank you for showing the interest in Sitefinity. Let us know if there is anything else we can do for you.
the Telerik team
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