Don't rewrite. Instead get yourselves Microsoft MVC 3 and learn that. - Since you already do asp.net you don't have to learn a new language, C# or whatever yo

Don't rewrite. Instead get yourselves Microsoft MVC 3 and learn that. - Since you already do asp.net you don't have to learn a new language, C# or whatever you currently use will be fine. - It installs side-by-side with your existing dev and production environments and you can use the the very latest and completely awesome Razor view engine[0] - Make a new version of a single ASPX page that you want to rewrite. Use the fancy URL rewriting features of MVC 3 to send some clients to the new version of the page while everyone else still gets to see the old one. - Upgrade your database to SQL Server? This way you bring your tech up to date without the risk of a huge rewrite. And you get benefits for your clients very quickly even if you can't help everyone at the same time. Even if there's always some legacy ASP pages left in your system, so what? If they still work then just leave them there. [0] http://weblogs.asp.net/scottgu/archive/2010/10/22/asp-net-mvc-3-layouts.aspx http://weblogs.asp.net/scottgu/archive/2010/10/22/asp-net-mv...