Maybe I should have mentioned why I jailbroke. The orignial question was did you jailbreak and how much experience do you have hacking pdaphones. It seems to have become a discussion on how useful apps from various sources are to people. So in that vain...
Jailbroken software I use in no particular order -
-I love skinning. - Winterboard is a great app for customizing the look of your iphone. Personally I like blueprint, Killsigncarbonred and vivid.
iPhone theme: Blueprint by ~sometoast on deviantART
http://iphone.sleepers.net/onepackag...ncarbonred&db=
http://www.appleiphoneschool.com/wp-...9/vivid102.png
-PDANet - Since you can't officially tether you have to jailbreak to get this software so you can use your phone as an access point for your computer.
-Intelliborn Intelliscreen - I missed my today screen from WM. Apple is adding features like repeat alarm so it may not be long but without jailbreak, you cannot write programs for the lockscreen.
Intelliborn™ - IntelliScreen™ - Your iPhone UnLock Screen on Steroids
-Categories - Scrolling through 9 pages of apps was taking forever. Now Categories is nice as you can put your springboard apps into folders. Unfortunately its slow to load folders but I only have 2 pages to scroll now.
Review: Categories (Organize Your SpringBoard)
-Cycorder - why this phone doesn't have video recording by default is beyond me.
Cycorder | Installer Apps | 3rd Party iPhone Application
-5 icon dock (Telesphoreo tweaks)
-Air Sharing has negated some stuff. Air Sharing is available in the App Store now. Its $6.99. I can do it for free but it took a lot more setup. Docs from cydia, plus openssh plus fish:// gets me there for free but for the majority of people its best to pay the $6.99. Both midnight commander and konqueror support fish.
Linux Online - Lesson: Goin' Fishin'
Andlinux is how I use konqeror on windows
andLinux.org -- Run Linux natively inside Windows
-ssh to your phone + terminal. This is probably useless to most users but I like manipulating my phone from commandline.
-iBlacklist - If this worked it would be freakin awesome but it crashes on my current system. Filters unwanted calls.
iBlacklist for iPhone
-Dock - Yet another way to get to apps
Dock - Ported to Firmware 2.0 | Apple iPhone School
-NES, PS and GBA emulators;macman(pacman clone with tilt gameplay); quake4iphone- I'm a sucker for old games.
-copernicIN - some kind of cut and paste.
-Orb currently not ported to 2.x software but I jailbroke the phone before I realized that this wasn't ported. It was one of the reasons that I decided to jailbreak.
-mxtube - download movies from youtube for watching offline.
Something I installed has destabilized my system but it could have been an appstore app but it is more likely its a cydia/jailbreak app. That is the downside. I am out of the sandbox and down the rabbit hole.
For me it was worth it, but as the debate has raged - YMMV when it comes to programs. Also I try to keep up with programs but really can't. For example, Air Sharing, there may be Appstore versions of what I have mentioned and I am just not aware of it.
I also have plenty of appstore apps but I didn't mention them here because you can buy/try read about it in the appstore and you don't have to do anything special to get them. So in summary - I've found plenty of useful apps from both camps.