[Vibrant General] Janis:
Coming from WM myself, (and just recently and very reticently turned over my beloved Wizard to my mom) the fun and unfun I have with Android:

Apps are so dratted cheap. Have at it.

Cloud connectivity. I use Picasa all the time now. It took me a while to get used to Google contacts, especially first name alphabetization, but I like it now.

You might want to look at subscribing to CompanionLink. It reliably syncs everything Outlook with your Google account (thus your phone).

Almost nothing was built into Android 1.0. Not much was added through 1.5. Some stuff has been added since, like Facebook sync, but custom ROMs don't add stuff. There's an app for everything. There has to be.

The app drawer is a hassle. I use FolderOrganizer (and ADW Launcher) to quell my addiction to organization beyond alphabetical.

It's fun to watch a few things catch up with WinMo and hear all the Android users brag about how great it is. Like app-specific auto-rotation. There's an app for it out now, but it actually costs something you'll think about, and it eats a hunk of RAM. They're just getting into animated GIFs. Lists and their apps aren't anywhere near ListPro, but they almost all have some way to sync to the cloud.

Office documents created on a PC don't always work with the Office apps that are out there. Don't bother with DocumentsToGo, but Sheadspreet is good (you have to convert first) and I'm trying OfficeSuite, and it seems the best. 30-day trial, $15. It's still not WinMo, though.

For those things you don't sync with the cloud, you can't just throw stuff in your My Documents Folder and rely on that backup. DropBox is a good app/service, and GoogleDocs is your friend. Most apps back up thier specific data to your SD, but on this phone, it's on the internal SD. You have to manually handle your backups, or do Nandroid backups (another worthwhile Google).

You have to install an app to install apps not from Market. Instead of exes their apks.

There's no Total Commander. :( I like Root Explorer. Astro is feature-filled. There are a million file explorers, and every one of them will have its advocates.

Flashing ROMs is tons easier, but you have to root first.

The Android world moves a lot faster. If you're off the forums for a week you'll feel like you've been in a coma for months. On the flip side, if you're waiting for something to get developed, waiting a few days feel like eternity.

Android devs work harder for a lot less, or no money; it's truly inspiring.

Before you go buying the first app that does what you want, check Market for more that do the same thing. I've found that there's a free alternative to almost everything. The paid versions/apps are more luxurious in one way or another, usually, but a little research can save you a bunch of regret.

Widgets suck RAM. Before you know it you've got 25 and you're wondering why your Home screen is lagging. Phones are finite. Even these.

CM is CyanogenMod. Google it, it's worth it. They started on XDA and it got out of control, so they have their own site now, although the threads still hanging on XDA re CM are a much more interesting read. It seems to be the most popular set of ROMS for a variety of devices. I follow and flash them (the ROMs, that is. I dont want the devs to hate me).

Double entendres are rampant. It's Google.

Once you get your apps organized, you'll be surprised at how smoothly your phone useage goes. Frankly, it's just more fun, and much cheaper, to play with.