The most simple way i have found to root my Motorola Droid "1" is to use Universal Androot. you can download that straight off your mobile internet from 4shared.com.
It just takes one click and your phone is rooted
I used it yesterday and so far it is working quite well. I may be a bit thick, but it took me like 5 minutes of looking around the developer's web site before I figured out what link was the download link for the program.
I was highly impressed with the ease of operation.
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