At my new job, we sell imported stuff. In order to be able to sell said stuff, currently the following things need to happen for every incoming shipment:
One solution to #1 is to send email to a Unix server (instead of Exchange) and use procmail to dump out attachments (see http://gimpel.ath.cx/howto_fetch_proc_metamail.html for an example of how)
As for boss, have a nice web page which you can email him a link to. And send him a short email (3 lines or less) telling him that using that page will save him 30 mins of work over the course of a month and you 2 hours of work in a month. Just be prepared to back up the #s.
However, very high level, un less you're prepared to do the whole automation thing on your own time, you better be able to sell your boss that overall time savings x6 months are less than time to develop this. 'cause may be monkey
salary in his eyes is low enough that the cost of software is just not worth it - and sadly he just may be right depending on how complicated a bulletproof robust solution is.