To make the transform work in development (using F5 or CTRL + F5) I drop ctt.exe (https://ctt.codeplex.com/) in the packages folder (packages\ConfigTransform\ctt.exe).
Then I register a pre- or post-build event in Visual Studio...
$(SolutionDir)packages\ConfigTransform\ctt.exe source:"$(ProjectDir)connectionStrings.config" transform:"$(ProjectDir)connectionStrings.$(ConfigurationName).config" destination:"$(ProjectDir)connectionStrings.config"
$(SolutionDir)packages\ConfigTransform\ctt.exe source:"$(ProjectDir)web.config" transform:"$(ProjectDir)web.$(ConfigurationName).config" destination:"$(ProjectDir)web.config"
For the transforms I use SlowCheeta VS extension (https://visualstudiogallery.msdn.microsoft.com/69023d00-a4f9-4a34-a6cd-7e854ba318b5).