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First, I don't think you want to use user categories. These provide sony-like collections, which are rarely needed in CC. Instead you create groups based on custom columns. It sounds like creating groups is what you tried to do.
Regarding grouping on custom columns: can you see the columns in book details? I assume you can.
To group on a custom column, the lookup key you enter in CC must be identical to the key used in calibre, including letter case. Your examples can't be right because they contain capital letters, which lookup keys never have. The easiest way to see the exact spelling of a lookup key is to hover your mouse pointer over the column heading in calibre. A popup window will be displayed containing the lookup name. Enter that name into CC exactly as displayed in calibre. If you want to enter more than one lookup key into CC, separate them with comma (e.g., #aa, #read, #genre). Press OK, CC will rebuild its database, and then grouping on those keys should work.
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