My iPhone 3g, keep the Jailbreak, or upgrade to iOS 4

Admittedly, I think that the jailbroken iPhone is awesome for all the wrong reasons.

I am a huge fan of hacked hardware. I have neither the drive nor the intellect to hack hardware myself so I have to rely on others to hack, then I just use their crap.

I jailbroke the iPhone for a few reasons:

1. Backgrounder. At first I thought this would change how I used the iPhone. Over a short period of time I discovered that I used this very little, then I realized I NEVER used it. Then I deleted it. Background apps sound really great, particularly using Pandora Radio, but for me, I never really found a place for it. Leaving this device, like any, constantly streaming audio over wifi or 3g drains the battery like free pudding at fat camp.
2. Winterboard. Being an artsy-fartsy guy I wanted the iPhone to look pretty. Prettier than it already did. This worked, there’s some battery/performance penalty, but it’s negligible and for day-to-day use it’s unnoticeable. Having 5-icons in the bottom dock is seriously great, as simple as it sounds it’s probably my favourite jailbreak perk. I’m easily impressed.
3. QuickReplySMS. I never bought it, it’s $3. I guess two things influenced my lack of purchase on this one. First thing I don’t trust the iPhone Hack Community with my credit card. I could have taken a big pain-in-the-ass route and used prepaid but that’s just ridiculous. To me, these apps are hacks, not in a bad way, but they are being written by someone who is circumventing an established paradigm to make money. This strains my trust. No offense, I’m sure you’re all wonder and ethical people, but it ain’t happening. Secondly, I don’t know if I will keep the jailbreak, so this may be money in the toilet.
4. Emoji. Turns out, this is already free in the App Store, who knew.
5. Emulators. These turned out to be expensive, the free ones worked ok, but I was not impressed with the performance or the fact that my big, fat sausage-fingers covered half of the screen and these games were meant to use an unobstructed screen. More...