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First, I would like to add this is not really a game-breaking issue, and I don't expect an immediate answer to this problem.

That being said, one thing I have noticed about the GOG version of RCT2 as opposed to the original CD version is that the CD version allowed someone to open a downloaded save file with custom content and automatically install the required data files, where as that doesn't seem to work on this version.

It's not a major issue, but I'm not sure why that feature doesn't work in this version of the game.
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ThatSolitaryGuy: First, I would like to add this is not really a game-breaking issue, and I don't expect an immediate answer to this problem.

That being said, one thing I have noticed about the GOG version of RCT2 as opposed to the original CD version is that the CD version allowed someone to open a downloaded save file with custom content and automatically install the required data files, where as that doesn't seem to work on this version.

It's not a major issue, but I'm not sure why that feature doesn't work in this version of the game.
How do you determine its not working? Works here.

What happens when trying to load a save/scenario with custom scenery for the first time is getting a little progress bar that fills very often, very fast and when it slows down and looks like 80% done the game throws an error and crashes. If you start it again and try to load that same file again, it only checks really fast and loads, as all the installing was done before the crash. Is that what you're seeing? That crash isn't gog specific at all, it had been in all the retail versions. But the installing works and it only crashes once per save.

The other thing I could think of... are you absolutely sure these files were saved with the export option checked? Maybe the uploader forgot, after all its not an option you keep using while playing on your own.
Nevermind. It just happened to be one file. I tried it on another one and it worked fine.