Ive spoken to people who have spends hundreds on apps from the apple iTunes apps store too. $3 for some of these themes out there is peanuts ! Take Noki HD for an example or Black UPS ! These are awesome slick themes that someone on stock can only pass a glance at.
Re springing takes seconds to do and is no different from when you have to restart your mac/pc after an update. It just becomes second nature. I just like downloading something and adjusting its settings and then eagerly awaiting the respiring to see the full effects.
Id love to be a fly on the wall in apples labs just to see what they are putting onto their own jailbroken idevices, raising an eyebrow and thinking ' shall we add this tweak to our own store' !!
Here's the problem with almost all themes. They only have a few icons of the millions of available apps. Of course they'll have all the Apple apps but if you have a majority of apps that don't have customized icons you end up with a half assed theme.
There are a handful of themes that render every icon, inPulse and Obsdian come to mind, that I consider as the best themes available. But even with obsidian, as cool as it looks it gets boring after a while. I honestly never got bored of the stock iOS theme. I think most developers put a lot of thought time and effort into their icons and most of the time it shows.
My point about respringing is that it removes the "it just works" part of the iPhone. Don't get me wrong. I enjoy some of the tweaks I installed and there are some very useful ones out there but I'm not going to go nuts waiting for a new jailbreak for the next iPhone like some people will.
If 5.1 gives me the ability to remove pictures from photo stream I'm going to be hard pressed not to update unless there's a Cydia tweak for it that I haven't heard of yet.
To me jailbreaking doesn't make the iPhone better, it makes it different. And different doesn't always necessarily mean better. Jailbreaking can be cool and useful but to me personally it doesn't matter that much. I loved my iPhone as much as I do now before I jaibroke it and I wouldn't lose any sleep if I lose the ability to jailbreak tomorrow.
Last thing I'll say is that some of the apps are really overpriced. Bitesmsm and iRealsms are two of them. They each add a couple useful features but $10 for either one is too much. If they were in the app store with more competition they'd cost no more than $5. Intelliscreen is another one. I bought it ($9.99) and it is not worth anywhere near $10. I don't understand why people rave about it so much. Especially now that you can get Bulletin for $.99 which gives you Notification center on the lock screen it's even more ridiculous at $10.