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Right now custom fields have 0 logic ability to them. They cannot push or pull data, you are not able to do any if/then based on the chosen options. I actually wanted to pull all of my department names into a custom field as a scrolling pick list cant even do that. There are a few open enhancements requests based on this here is the main one (Custom Field Logic )
As to your second question you can tie Assets to users and departments so that might work for you
Thank you for your feedback, typhoon87.