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I consider myself a "dumbass" at times.....

The folks around the android community have made it amazingly easy. +1000 to all of them. There is still some risk so be aware of that going in, and be willing to accept "your" actions.
I followed this guide, with the only difference being that I chose bugless beast V0.4 rather than the saphire rom that they used. Read it a few times, and watch the videos a few times. After that, if you feel comfortable, the choice is up to you.

How to: Root Android 2.1 and Install Android 2.2 on Motorola DROID - Droid Life: A Droid Community Blog
 
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The folks around the android community have made it amazingly easy. +1000 to all of them. There is still some risk so be aware of that going in, and be willing to accept "your" actions.
I followed this guide, with the only difference being that I chose bugless beast V0.4 rather than the saphire rom that they used. Read it a few times, and watch the videos a few times. After that, if you feel comfortable, the choice is up to you.

How to: Root Android 2.1 and Install Android 2.2 on Motorola DROID - Droid Life: A Droid Community Blog

is that better than this?

How To: Root the Motorola Droid (Android 2.0.1 & 2.1) | TheUnlockr
 
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its simple! very easy..just follow these links:

start here: step 1


then here: step 2...
Download Froyo (2.2) for Your Motorola Droid ! ! !


then you can install a rom... here's what rom i use.. Bugless Beast

then you can overclock .... i used this one... ChevyNo1 ulow v 1.1 kernal

then add a theme... i used this.... NexTheme


and....you can change your bootload animation for kicks.... mine..

6060d1270783097-new-droid-peeing-apple-boot-animation-droid-pee2.gif




have fun! its all easy...make your phone unique...this isn't an i*hone....DO WHAT YA LIKE! :D
 
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I don't know. It seemed like the one from the unlockr had you go back to 2.01, then to rooted 2.1. While I was agonizing over doing the procedure from unlockr, the droid-life procedure came out and was going from 2.1 stock to 2.2 rooted in one shot, so I decided to try that one. Worked out well for me at least.
There's tons of these guides out there. Read many of them and do the one that makes you feel comfortable.
 
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Wireless tether is free, unless Verizon catches you. :p ROM Manager has a free and paid versions. I think the free version will not allow you to automatically download and install new roms from within the program. What that mean is if there is a new ROM you want to install, you will have to download it and put it on your SD card manually. I got the paid version just because they made it so easy. You have to support the community. :)
 
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tethering apps free...rom manager helps you install roms easier...also type in root in the market and you wil find some more apps for rooted phones. also downloading Titanium backup is a good idea, it backs up all user data, app data, very important to do a backup before you try to install any roms,themes or anything else. also reboot into SPrecovery, hold x and power, and do a nandroid backup too. you can never have too many backups!!!!
 
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