Honestly, I've found that Windows doesn't "just-work" for me. Before I switched to using Linux for most of my stuff I was a Windows person. For it to do what I wanted, I had to hack around with the system way to much (occasionally messing it up) and having to reinstall (didn't know how to restore an image succesfully yet). Then came Vista, what I necessarily knew no longer worked, and after a few months I gave up, heard about Ubuntu. Gave it a whirl and now I'm in Ubuntu most of the time.

Maemo is kinda similar. While I don't find it ideal [there are many many improvements that could be made], there aren't any other alternatives out there for me. I could go with a Windows based one, but from my experiences it's left a distaste in my mouth. And I really don't feel like hacking around with a Windows machine anymore. I was considering an iPhone, but the price plus the fact that I'd have to jailbreak it and deal with updates and all that jazz just to get it to do what I wanted it to do felt kinda pointless.

Maemo is kinda like that.. for example, rotation. It had to be re-hacked everytime there was an SSU update. But at least it's not as bad as what I would have to go through if I were using an iPhone.

Like I said earlier, each user's experience is different. My dad owns a TomTom GPS. I used it myself for several roadtrips, that itself has left an occasional distaste in my mouth and I find that MaemoMapper does a better job as long as you download the maps beforehand. And since I don't have a data plan, it requires me planning the route beforehand. The only experience I've found that's better was when my cousins and I navigated a road trip with his iPhone 3G. And I thought that was pretty cool, though the fact that Apple won't allow background apps and your stuck with Apple's restrictions unless you jailbreak it (leading to my point above) kinda killed it for me.