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:
I'd start by asking myself the following questions
Just some thoughts.
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.
There are lots of tools that you could apply here, including Python, Excel macros, VB Script, etc.
In this case, PowerShell seems like an excellent choice, as it naturally combines COM access to Office, .NET, and scripting, and is all-around-awesome. If you already know a suitable technology, you'll get the job done fastest with what you know. Othewise, PowerShell.
(C# 4.0 is also reasonable, although earlier versions suck when interacting with Office's COM interfaces.)
Don't get carried away trying to solve the whole problem at once. Start by picking a small, easy part that gets you a lot of value right away. You are more likely to succeed this way. (To get your boss to agree, you need success fast. If you aren't telling your boss, you need success even faster!). Once you have that done, you can use your new-found free time (maybe only a few minutes per day) to extend your tools and skills to the next bite-sized piece. Success will accelerate success.
In time you will replace monkey with code, and either get a promotion or quit in disgust and get a better job.
As I noted above, your last question is probably the most salient. It is probably best approached as a personal skunkwork project where you show the boss a completed product one day, collect your innovation bonus and then get fired because a stupider monkey can now do your job instead of you.
The big parts are Excel and email. Excel can be handled with either COM or some sort of interaction with OpenOffice.org. Email, well, there's dozens of ways to do it. My hammer of choice is Python, along with pywin32 or PyUNO, and poplib and smtplib.
Boss... will always be boss. Not always very much you can do about the icky wetware stuff.