Starting to lay out a web app and need to decide on language
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1) server-side language
2) a book on structuring such a web application
I'd prefer things that play nicely with linux - I've used and have an extreme distaste for ASP.NET or applications written using the like.
If it doesn't run behind a firewall, you'll probably do the initial deployments into the cloud and will want to qualify your choice for suitable such platforms, too. (For instance, for Rails there is Heroku and Engine Yard.)
If you can be more specific about exactly what you want out of a programming lanaguage, it's possible to give a more objective answer.
For item 2, structuring a web application, you'll also want a good book about user interface design and web usability. I'm a fan of the works of Jakob Nielsen and Don Norman.
The hard truths:
You may end up throwing your first version's code base away, particularly if you're using a new technology (to you) for implementation. This is especially true if you have to do much performance optimization.