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The simple fact that you are using conditions seems to warrant different copies of the WebHelp output in different locations.
You might try explaining it to your server guy this way. Think of WebHelp output as being like a batch of chocolate chip cookies. You have one batch that is plain. Another batch with walnuts and another batch that uses pecans.
Think of each server location as being like a cookie jar. There is no way to have all three batches in the same cookie jar and make it work.
Yes, you are correct in that all the cookies share some of the same ingredients such as flour and eggs. But each batch is a unique mix of those ingredients. Thus they must remain together as a unit.
Hopefully that helps. And I've been accused of using "sexist overtones" in my analogies. Please know it wasn't meant in any way to be sexist. It's just that sometimes by thinking about things in different terms they are simpler to explain. At least I think they are. Many seem to agree. Especially when folks don't understand about all the silly RoboHelp files.
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LOL, clear as day to me and it didn't occur to me that it might be sexist! A good analogy works always. I will copy and paste it to my server guy.