I do just that thing myself! I run Windows 7 x64 with Outlook 2010. I use Google Calendar Sync to synchronize my calendar and contacts with my GMail account.
Then my Android Tablet natively syncs with my GMail account, so it has those contacts and calendar entries.
And my WinMo phone connects to my GMail account as well to sync contacts and calendar.
This allows me to enter a contact or calendar appointment on my Win 7 laptop, my Android tablet, or my WinMo phone, and within a few minutes the entry has been propagated to the other devices, seamlessly. VERY slick and easy to do!
Also, consider SugarSync - I use it as a common “share” between my laptop, tablet, and phone (and any other computer I may borrow). A common 30 GB storage that’s accessible from all platforms. Nice to drop my presentations and latest docs I need to share there (typically PDFs and the like), so no matter where I am, and even if I have just my phone, I can still access what I want and show it/share it as needed.
I guess Bill Gates is telling me, if I want a smartphone, I need to upgrade to the Android or go the iPhone route.
Android does NOT have a subscription requirment ala Apple, correct? I have no need or desire the surf the internet from a cellphone.
I guess I really need to find some resources and read up on these new devices.