Topic: Ruby and local environment

to start off I'd like to say this has been a great resource and it's definitely helping me improve my rails. However I feel like I've reached a wall.

To start off with my problem:

We are a multi OS environment. I need to create an app that will accomplish a couple of things. The main purpose of the app is to upload a file from a local environment and store it on a created folder on a server. Preferably using a droplet or drag and drop.  My problem is I need the app to integrate with outlook so the user presses a button and the email get uploaded to the server. I also need it to integrate with filemaker so if it's a new entry in filemaker the app will take that entries ID number and create a folder on the server.  I need it to rename files and generate html files from specific layouts with the information automatically when uploading. Does win32ole work with rails??? Can the web app access a local OS.

I know this is a lot to ask for, but I would really appreciate some of your advices.!!
Thanks in advance,