1) If you put the time in to get the phone set up, and buy a few apps the phone will do both better than the blackberry, imho. I don't really get the "Business" or "Fun" phone. Blackberry's can be fun too. (I know this is the android forums, so we'll pretend I didn't just say that last line.) A truly good phone will do both aspects well. Which I do all my appointments, emails (non-exchange), and calendar management from my phone.
2) If you wait until after the update is released make sure the store shows you that it is 2.1 before leaving. If a particular store has leftover stock they will still have to sell those and I doubt they update them especially if it is a third party retailer.
3) They are apps on the market that do outlook sync but that will cost you. gSyncit will do what you are asking of it but you are going to be paying $15 for the app.
4) Not unless you get a lemon.
5) I work in a building that gets terrible reception and this performs well as my old Centro in signal which was decent.
6) I sell the sprint service through Radioshack. There is no difference in the plan on either phone. For a family plan 1500 min for landlines and roaming calls, anytime any mobile (free calls to any cell phone regardless of carrier anytime), unlimited txt, unlimited data, navigation, and a few other perks (NFL, Nascar, Sprint TV and etc.) for 129.99 month covering two phones and 20 bucks a line for 3-5. The only difference between the moment on the plan is the plan code I assign you setting you up. Though you being the customer you wouldn't even realize it.
A little extra tidbit. If you want something that is going to work out of the box go with the the new curve or the tour. Though if you want something that ultimately be more powerful and customizable go with the moment. It's just going to require a little bit more tinkering than the blackberry.