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I just thought I would come up with a list of some of the great things about jail-breaking an iPhone.  Please please PLEASE: See the note below the list before going ahead and attempting to jailbreak your iPhone.  I won’t give any links or instructions on how to do a jail-break.  That part is up to you…there’s plenty of web sites and forums and videos out there that show various ways.

8 Reasons to jail-break your iPhone:

1. Alternative keyboard configs! I absolutely hate the standard QWERTY keyboard.  I type with DVORAK on my PC, and it is so much easier on my fingers and hands…and I don’t get carpel tunnel.  I downloaded a free DVORAK keyboard config for the iPhone and BAM… now typing on the iPhone just became a lot easier.
2. Blacklisting apps which allow you to completely block unwanted or unsolicited calls. (cannot be done with regular apps on a regular firmware.
3. Ability to install customizations such as the SBSettings feature.  It lets you set up simple on/off switches in a very accessible place that you can usually access from most apps.  This is very nice to enable or disable the phone, or tethering, or the wifi, or data network, or SSH, etc.
4. Alternative phone service through VoIP providers.  This can work through a SIP app that can be installed, which the best one I’ve found isn’t available from the iTunes store: Siphon (FREE).  You can save your minutes by using this!
5. Tethering your internet service on your iPhone to your computer!  I don’t use it a lot, but when I need it, it’s sure handy!
6. Further customize your icon dock to have more than just 4 apps.  I have 6, and although it’s crowded, I much prefer it this way.
7. Exceptional apps that Apple doesn’t approve of.  Some apps are really great and for some reason unknown to man, Apple decides not to allow them.  Probably because they would take away from their market share.  At any rate, some apps are hard to live without.  The OpenSSH (secure shell) app being one of them.  I can get into the inner workings of my iPhone and transfer files in and out without hassle…all done over WIFI.  This is very useful when I’ve got apps like Cycorder (free video recorder for the 3G) and need to copy the videos off.  The iFile app actually provides a half-way decent PDF reader which makes a GREAT alternative to the built-in PDF reader on the iPhone.  This way I can read my eBooks from my phone the way one would read a book on a Kindle.
8. The obvious reason to SOME might be that you can install cracked apps.  While that can have it’s advantages, you must be careful not to get ones with viruses, and sometimes the apps come corrupted or something and might just simply crash on you.  It’s a risk you must weigh yourself.  Also to be noted, the place for downloading the cracked apps which was the safest and most official, has stopped offering their repository of iPhone apps.  So that’s another thing to consider.

With all of this said.  Please don’t go out and just try and jail-break your iPhone without doing some research or consulting somebody with experience.  I would hate four you to brick your phone on account of my suggestion because you didn’t find out that you had better not do it a certain way with your particular model or something.  From what I understand, you have to carefully consider jail-breaking an iPhone 3GS because it can mess things up, or even cause it to have to be booted from a special app on your computer if it gets turned off.

Personally I’m glad I don’t have the 3GS, because I love the way my phone works as a lovely jail-broken extension of ME.