I've got an iPhone 3GS and my girlfriend has a Droid Eris with Android 2.1.
The difference in the app stores is honestly night and day. Apple's App Store is full of richly-designed and functional software. Unfortunately you also end up paying $3.99 for a halfass paint program that can't even save. Sure it's "elegantly designed" but so fucking what?
Most stuff on the Apple App store is well-done yeah, but so much of it is corporate stuff. Lots of $5 games that still nickle and dime you for extra levels, "free trials," and the like.
Don't get me started on jailbreaking. I tried it. The software available is of notably inferior quality.
Updating is semi-manual. I kinda like that because it means that you won't end up with an update getting pushed out to you that removes features from an app. Believe me, a lot of app developers are in love with intentional regression bugs. At least in updating you can look through each app and read the changelog. Appler requires the changelog be posted so users can see it. if you don't want it, don't update. If you want all of them, you can select "Update All."
Android Market on the other hand sorely lacks anything of value that I can see. The user experience for the apps is a hodgepodge of decent through to downright awful. Most of the software is free, but it's patently useless, sometimes not even functioning properly.
Updating is even worse. It'll inform you of updates via a tiny icon in the status bar at the top which you have to grab and pull down like a drawer. Then you have to update each app individually, waiting for each one to finish before going to the next.
I guess in the end the analogy continues.
iPhones, like Macintosh have some high quality software that you won't get away without paying $50 for. Want a simple word processor? $49. Want some graphics software? $89. Want whatever? Well, odds are it won't be freeware. You do get what you pay for though. The money you pay gets you a higher quality app than the scores of freeware available for Windows.
The truth is that in 2010, Windows is actually pretty good from a speed/stability standpoint. Windows software I think will always be garbage though. Developers just don't seem like they could care less about UI design, testing, QA, or even quality coding. It really seems like a great deal of the software on the Android Market is this way. Google doesn't do any checking, so someone could just put a half-finished app up there that segfaults every time you tap the button to make it do something and it would stay there.
Disgraceful really :p