1) The stock e-mail app handles hotmail fine, but since its IMAP, read messages on device show up as unread on-line still and vise versa.
2) Personally, I hated the Pre (Current Hero User). You can multitask in Android, but the visual part of it is better on the Palm, but the device is built so poorly, it doesn't even matter. Plus, on the Palm phones, Browsers have to refresh if you go back to it from another app, Android, you don't, it keeps it right where it was. Theres a shortcut feature that allows you to jump from the last 6 apps used. As far as the notifications, I get a lot more in Android. The difference is that Android puts them on top, WebOS puts them on the bottom. Functionality wise, they are equal. Just drag down the slider and boom, there you go. WebOS you tap the area and it expands. Not a whole lot of difference there.
3)Yes, from what I've heard, it looks nice. I'm a mac owner now, but I loved Rhapsody when I had it on PC. It has a free trial too, maybe you should pop into one of the stores (T-Mo, Verizon or Sprint) and download it and see how you like the interface. There was a review of the app if you want to check it out (may still be in beta).
4) Nothing can compare to the Blackberry speaker phones! I'm jealous as well, however, its pretty loud on my Hero, which is another HTC device.
5) Yes, though, not through BT (maybe on N1, but definitely not prior to 2.0 on older devices). You can even use google search using your voice. If you don't have a thick accent, it actually works quite well.
6) No, not an ESPN app. There is a pretty sweet app called SportsTap that has widgets of your favorite teams and gives you notifications on the score as it goes on. It was a bit behind actual time, but if you aren't using it play-by-play, it works well.
Extra's:
Widgets are awesome. The N1 is ridiculously fast. Palm's Hardware SUCKS! One thing you have to remember with multi-tasking. If it involves the internet and a phone call, WebOS currently cannot do it unless you are connected to wifi. Thats a limitation with CDMA phones vs GSM. I currently am a CDMA user, and I will continue to be one, unless I get a job where I HAVE to go overseas a lot. Copy and Paste is much better on android devices vs WebOS, but a little less convenient than the iPhones. They keyboard on my Hero is fine, but it won't be as nice as the iPhones (I had a touch and did like the responsiveness of the keyboard on it.) If you're really lazy, you can just have the phone do it through voice.
WebOS currently doesn't have any API's in its framwork to include the camera or mic. They will get video recording and editing later this month, but still no mic support, so no voice recording, no voice dialing, no apps like shazam that can tell you what song is playing. I was a hardcore WebOS user until I went through 5 phones, and got tired of waiting for basic phone functions to be included, on top of the subpar antenna on the device. You can do bluetooth data transfer on the N1 with an app called Bluetooth File Transfer. Bump works Cross-platform. Many iPhone games are coming soon as most can just be ported over easily by the company the developed them. The only limitation currently is the internal storage. With root/rom, this is a non-issue as you can store the apps on an SD card and have the space only limited by the size of your SD card. Don't bother with Class 6 16GB cards. If you can find it cheap, go for it, but class 2/4 work just fine for the price.
If you have any other questions, let us know.