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There’s a way to make it so intellisense will behave appropriately for custom data-types in a similar way, for example, variants will display VT_I4 for a variant that is of type “int”.
I’m trying to get intellisense to be more useful for my custom array data-type. So another similar case is the vector class, how it shows its contents appropriately and I don’t have to use the Watch windows to access different elements.
Have a look at the file autoexp.dat, and add entries to this file for your own datatypes.
The following explanation helped me a lot: Writing custom visualizers for Visual Studio 2005. The file itself contains a lot of documentation about the format as well.
VS2008 and VS2010 use the same file and the same format.
BTW: I recommend to make a backup of the original file before you start modifying it.
UPDATE: Searching for autoexp.dat on SO reveals a lot of information. This answer has several more links.