Contact Sync Best Practices?

I've been asked by a friend to help sync his contacts with Outlook 2010. He currently uses a Gmail account which connects over the air with his iPhone 4 using ActiveSync (mail + contacts + calendar) and he wants to see the contacts on Outlook. I plan to setup the email account in IMAP mode.

My past experience with synchronizing stuff with Outlook has been absolutely disastrous. Only Exchange equals trouble-free in my book. I consider iCloud because I assume that enough QA effort went into it and hope to be pleasantly surprised. But if the consensus is that it is not ready for prime time please let me know...

Anyway, before I begin I would apprecaite your thoughts on the following:

1. Would you advise to turn off ActiveSync synchronization for contacts if I turn it on in iCloud? That way avoid the greater risk of three-way sync between Gmail <-> iPhone <-> Outlook but Gmail would be taken out of the loop.
2. Is it possible to use the same iCloud login on TWO computers without truble? So we can have the same contacts on both.
3. Is it possible to set the iCloud contacts folder in Outlook--once created--as the default location for NEW contacts as they are created on Outlook?

Thanks