What's your operating system? If you're on OS X, the external stuff sounds doable using AppleScript.
Yes, I'm in OSX. I thought Applescript would connect the two, but I'm not sure exactly how to build an Applescript command into a button script. I guess it's time to RTFM.
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I guess it's time to RTFM.
Yes, that too …
I was thinking that you could use a droplet for the drag & drop part; pass the list of file names to FM, where you use a simple looping script to create the records (and maybe tag them at the same time). The thing to watch out for is (as so often) error trapping, in this case preventing the creation of duplicates.
As far as tagging is concerned, you may be able to save yourself lots of (selection) work by parsing the filename (and/or its path) for tagging metadata.
Opening a file in its parent application would be simply an “Open URL [ fileName storedInRecord ]". Not sure yet how you would get a file into the frontmost window of an arbitrary application, but it probably isn't rocket science, either …