Earlier this year I wrote a small article for developerFusion about using Windows Azure Web Sites, Cloud Services, and Virtual Machines. It is a fairly introductory article, but I think it shares some nice ideas on starting small with Web Sites and growing into something bigger and more architecturally complex by using Cloud Services or Virtual Machines.
I meant to post about it here when the article was published. But, crazy me, it slipped. Check out the article today at http://www.developerfusion.com/article/148148/the-evolution-of-a-azure-web-application/.