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I have a road that I want to create multiple annotations for. Is it possible to attach more than one annotation to the same feature?

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I don't see why not. Define labels export to annotations, turn on the dynamic labels again, edit as needed and export to another annotation class. – Jakub Apr 21 '11 at 1:13

I'm not sure what the setup is for ArcGIS 10, but in 9.3.1 on the Properties>Label tab you can define more than one label class for labeling. Change the "Method" option to "Define classes and features and label each class differently." You can then define a different field, placement properties, and expression for each class. Alternatively, you could just only label one class, but concatenate multiple fields within the expression option (see example below).

[FIELD1]&" "&[FIELD2]

After you have your labels setup and labeled you can then convert them to feature linked annotations.

In addition, the ArcGIS Resource Center has much more literature on labeling and annotations.

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You can control pretty well every facet of annotation behavior (placement, font, color, add symbols, rotation angle, multiple labels per feature, etc, etc .....> ).

....and yes, create your different annotations and organize them in a geodatabase.

Better explained by ESRI actually. Everything you could want to know here

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