Exchange 2010 Certificates, IPs, and Domain Names...

I'm setting up a new Exchange 2010 server, migrating from an old Exchange 2003.
I'm at the point now where I'm stuck and cannot move the mailboxes of the users to the new server until I get the new server setup with certificates, reconfigure the firewall, and more Aname records. ... reason, I'd like to take advantage of the autodiscover,
sync, outlook anywhere, etc.
I've been tossing ideas around but I think I'm over thinking this entire thing on domain names, anames, certificates, etc.
Can someone tell me what the best practice would be for creating the CSR? And I'm a bit curious as to IPs.
While the examples in the New Exchange Certificate wizard all show 'mail.contoso.com' I wanted to be more specific on the functions of each but maybe I'm causing myself a lot of extra work. Each full aname needs pointed to a different public IP from my understanding
of the certificates. Can anyone tell me if this approach(below) is best practice or far from it?
I'm very intrigued with the capabilities but dont' understand why MS would use as an example the same domain name, mail.contoso.com for each function. But it may be because they'd just have to point to one IP address whereas I'll have to point several IPs
public to a single IP internal.
I'm just asking for suggestions... and ideas... and how you setup your exchange 2010
I was going to create:
Outlook Web App:
webmail.domainname.com,domainname.com
Sync:
sync.domainname.com,domainname.com
Autodiscover:
domainname.com
Outlook Anywhere:
outlook.domainname.com, domainname.com

Not sure I understand - but why do you want to map each individual service to an individual public IP ? Usually the trend is to keep as little public IPs as possible (you can get away with 1 public IP for the CAS role). For autodiscover, I've usually seen
the autodiscover.domainname.com being used, due to the domainname.com reserved (public site) - this actually keeps inside the logic used by Outlook clients to autodetect the servers (see
this link).
As for the Subject Alternate Names (SANs) on the certificate itself - it all depends whether you're publishing the server directly (in this case you'll want to get away with as little SANs as possible) or you'll use a reverse proxy (TMG/WAP) to publish the
internal box (in this case the certificate on the reverse proxy can contain little SANs, but the internal server can have SANs map to each service if you want).
Also - Allen's link is a definitely must read.

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    "Courage is doing what is right."
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    >>>
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    This posting is provided AS IS with no warranties or guarantees , and confers no rights.
    Ahmed MALEK
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    My Linkedin Profile
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