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Sounds like you want a 'dynamic image' like 'dynamic attributes' - this might be a starting point: From ArcGIS Pro's help: Dynamic Image Insert dynamic pictures with Map Series If you are using Map Series, you can make your picture element dynamic and have it update for each page. To do this, double-click the picture to open the Element pane. ...


You have to georeference the raster first. Its not just about a CRS, but the extent of the raster (in CRS units) too. You make yourselve double work if you digitize data from the raster, and then try to adjust that to reference maps like bing. There are a few tools to georeference vector data, but you will not have the convenient "pick from canvas" tool.

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