There's a program I've used before that can automate almost anything -- even website inputs, etc. Auto Hot Key. We've used it at work to end tedious data entry on some back end sites we use. I don't rememeber if it can do EVERYTHING you're looking to do but I *THINK* it can. It's a really cool program. You may have to write a macro with it and then call it with task scheduler. Could be pretty easy to do, actually. Here it is:
http://www.autohotkey.com/
How about VB -- do you have / know it?
- Jeff



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