James,

It really depends on how many documents you're talking about. But.....

In the past, I had used a table (so that it would be easy to change the file location in the even of a data migration) to link to the documents called out spatially via a polygon. So basically, join on that table to pick up the file location. You can do this just the same without georeferencing if your asset management system has an excellent search tool. The added benefit of using a table (access is nice) would be that you can add search identifiers and the like, consumed perhaps from existing data.

This was a successful method in the Flex environment as well as html5 utilizing geocortex. This also worked in Vueworks, which is a pretty clunky asset management system.

I would advise doing the bulk of your work in ArcMap. If you want to spatially reference your documents, you can get clever geoprocessing to find things a "home" in a near automated process. Besides, it's easier to go with what you know and then transition to what you don't know so well. Just make sure you set everything up with your needs and capabilities in mind. It really all boils down to the capabilities of your asset management system, what type of data it can see (joins, views your database admin might set up for you to consume, etc.). In the end, I think this route lends to greater flexibility as it puts the ball in your court, so to speak, and shouldn't limit your capabilities down the line.

Good luck!

Michael Ray