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:
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.