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What is the file path for the Vst folder you use for your Vsts in live? The Blackhole installer installs two .dll files:
32-bit: C:Program Files (x86)Common FilesSteinbergVST2Blackhole.dll
64-bit: C:Program FilesCommon FilesSteinbergVST2Blackhole.dll
Do you have Live pointing at the 32-bit file path, or did you move it to another folder that your other Vsts are in? I'm guessing that you might have moved the 64-bit version of the plug-in to a custom plug-in folder that you use for Live, in which case it won't load. You'd just have to put the 32-bit version in that folder to solve the issue.
Please let me know if that is not the case.