> Problem 1: I need a distribution list of 500 Contacts, I am unable to
> generate a list beyond ~100 Contacts due to the "maximum size for my
> network e-mail server" .
Outlook itself has no maximum size for DLs. If you are receiving an error
back when you attempt to send a message, that error saying that you have too
many recipients, then the fault lies with your ISP. Speak to them about
allowing a larger size on their SMTP server. Barring that, consider mail
merge or some other mass mail tool.
http://www.slipstick.com/addins/massmail.asp
> It's painful to go through 500 Contacts picking SMPTs and ommiting Fax
> Numbers... If I write them to Outlook, I can select the email
> addresss and paste them into the DL, but then I'm not really
> connecting the Contact with the DL.
Adding members to a DL does not connect them to contacts, no matter how you
add them. And I don't see how you "omit" anything. Just don't select the
FAX mail type when selecting your entries in the Select Members dialogue.
Widen the Address Book window to see the mail type to make it easier to
distinguish ot simply select the first name in the list if you see two
identical names, since the FAX entry will always appear after the mail
address entry (or entries).

Signature
Brian Tillman [MVP-Outlook]