[WaseemAlkurdi]

What I'm looking for is experiences with jailbroken Kindles. Why did you want to jailbreak?

I jailbreak primarily to use KOReader and its built-in PDF reflow (otherwise PDFs are unreadable), but also to completely use the small low-power ARM computer that I have paid for. The Kindle runs a custom Linux, so you can leverage that to run a "standard" Linux on top of the Kindle's Linux, which gives you a pocket Linux computer with a Kindle's worth of battery life at a very reasonable price.

Is it only for the screensavers?

That's a good incentive, but not really.

And now that you've jailbroken your Kindle is it really what you'd hoped for?

Not only did I get what I hoped for (and more), I can't even stand using a non-jailbroken Kindle anymore. But maybe that's only me.

And is it easy to maintain the jailbreak?

Yeah. Turn off Wi-Fi (so that no surprise updates arrive), or use a dummy "update.tmp.partial" file if you really need Wi-Fi.
If an update arrives (or you really want a feature from an update), you're most likely going to see a "heads-up" here on the forum if the update is "dangerous", in that it wipes your jailbreak. But that's never happened (AFAIK) until very recently with firmware version 5.12.x.
And have a serial adapter handy. If you have one, then no update on Earth could stop you from downgrading. At least that's if Amazon doesn't do something to remotely butcher our serial ports. (The name "serial adapter" strikes fear into the hearts of many, yet using a serial adapter is really as easy as charging a phone).

Or do you regret is because it's a lot of hassle?

Not at all! ;-)

I have this voice in the back of my head saying I should jailbreak once it's possible, but on the other hand, it it really worth it? If it's only for the screensavers, I can live without those.

You won't lose anything by doing the jailbreak.
Even if you had to open up the Kindle, you're going to find out that the whole serial jailbreak process is nothing harder than playing with Legos.
And if you don't like the jailbreak, an update followed by a factory reset is enough to destroy any remains of a jailbreak.

On a Kindle, a jailbreak is simply copying one file, called a developer certificate, with which the main jailbreak apps (the KUAL app launcher + MR Package Installer) are signed with.
A jailbreak is exactly like telling the Kindle: "Look, I know you don't like these non-Amazon apps, but as a favor between friends, let them run, alright?"