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Choosing a Server-Side Scripting Language - Criterion 1

I’m spent the last couple years building a platform based on ASP.NET, and I’ve come to the conclusion that it’s not right for my needs.  I’ve thought hard about making the leap to PHP, but I want to do so with my eyes open.  Ruby seems like a reasonable alternative, as does Python.  (Who knows, there may be another option that I’ve failed to list.)

I've broken this question into several parts simply because it's so big.  This is my first (and most important) criterion:

Criterion 1 –  I want a server-side scripting language on which I can build a reasonable level of abstraction.  If I hire a new contractor with a solid background in the language of choice (PHP, Ruby, Python, or something else), they should be able to understand my platform after a few good hours of explanation.  .NET’S Entity Framework is a good example of what I’m not looking for.  I took a crack at implementing it into my ASP.NET platform, and it was simply too abstract for me and my contractors to work with effectively.
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Aaron Tomosky
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Agreed.  All references to .NET in my existing framework are C#.NET.
Right, so the problem with leaving .net is you are leaving c#, .net, mvc, razor, visual studio, and usually iis (you can run php in iis but most things like Drupal don't really play nice without apache. You have to manually do things like redirects in web.config that it would expect to be in apache .htaccess
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A point of clarification: I'm going to make no effort to use the .NET elements associated with my previous framework:

Visual Studio - Won't use it.
IIS - I'll switch to Apache.
Telerik Controls - Gone.
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Another way to test and have a dev environment is turnkeylinux.org and free VMware player. They have ready to go lamp, ruby, tomcat, whatever servers.
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Thanks to everyone for the terrific feedback.

aarontomosky - I really appreciate the framework comment.
DaveBaldwin - Thanks for XAMPP suggestion.  It's a good one.
smadeira - You make a great point about reconsidering .NET.  Leaving it behind is not a decision I take lightly.  (I still may stick with it.)
Slick812 - Terrific comments.  Thanks.