Outlook and the iPad (or other computer, for that matter)

Your decision tree looks like this:

Do you want to stick with Outlook or go to something else?

I.  Stick with Outlook:

Advantages:
1.  You may be able to install Outlook yourself- no cost for installation.  There is some risk.
2.  You will have an environment that is somewhat easier to learn;

Disadvantages:
1.  There will be a learning curve over the 2003 version, since the new outlook has a ribbon interface and some important functions have been moved around enough that they are hard to find- sometimes even help isn't that helpful. Tthere will be some trial and error or time spent watching the tutorials, even for he experienced Outlook user.  (Maybe I should say "especially for the experienced Outlook user.)
2.  The initial software cost: is over $100.

II.  If you don't stick with outlook, there are a number of "free" alternatives.

Advantages:
1.  No software cost
2.  May actually open up additional functionality and convenience.

Disadvantages
1.  Learning curve, though perhaps not as much as going from your current version of Outlook to a new version.
2.  You may have to pay for installation- transferring the outlook database, contacts and calendar to the new environment.  This depends on your skill and patience.

Three to mention:

1.  Windows Live- the replacement to Outlook Express, has the standard function of the old Outlook.
2.  Thunderbird- an opensource alternative that is highly configurable and more function than outlook... if you want to learn to use the new function.  But "out-of-the-box this looks like a fancy version of 2003.
3.  Google- In general, this would be a web client.  However, if you want quick download and disconnect, then you would want to fire up a client on such occasions.  One such situation is when you are on a cruise. Then you could use any iPad email client.  Google is my choice for web email client, even if your ISP happens to be AOL or ATT.  That is because it is "light:"  not a lot of ads and expecially no animated ads; and it has a lot of configuration features that link with email clients and Google Desktop.

III.  Not worry about synching to your outlook database at all.

Assuming you have an iPad email client, create the POP3 account for ATT, the same way you did for Outlook. Upload your contacts list to ATT on occasion to keep it recent.  Download it to your iPad email client.  Then turn it on.

Note that both your Outlook and your iPad email client would be set to delete from the ATT database only when the Delete folder contents are deleted.  This would keep the two clients somewhat in synch.  (This assumes the iPad email client has this capability.)

I've read something about the standard iPad email client:  http://www.ipadforums.net/ipad-help/17767-email-options.html.  You might read through that and maybe another client would be better for you.  In fact, Thunderbird- option 2 above- is one of those, leaving me with the thought of good fung shui, since both clients are the same.

I haven't followed through on what goodies Thunderbird offers for synching multiple instances of the database.  Usually someone will develop a utility for this.  But synching email isn't necessary when the clients are configured to leave on the server and then delete when the delete folder is emptied.  Synching contacts can be an issue, but this can be overcome with a web client like google, which can be considered the golden source, and the client synchs to that source when downloading.  (Possibly you would have to start this process manually, depending on the capabilities of the client.)

OK, so assuming you go with an Outlook upgrade:

1.  You can get Outlook separately or as part of the Office Pro package.  Always get the latest version.
2.  There are three  on-line places to shop around here, in addition to just typing "Outlook 2010 2011 prices" as a search phrase.  These are:  Microsoft Store, Amazon, and Costco.  Don't expect the prices to vary more than 15%.  Sometimes Microsoft will have a special one day deal, like the time I was able to get a Dell Netbook free with the purchase of an Office Pro license.  
3.  Always do the download, if available, AND get a DVD.  The latter is important when trying to recover from a crash or transferring to a new machine.
4.  There are two configurations to every Office deal:  a card and the full package.  The card is a license for only 1 machine.  It is often somewhat less expensive.  The other is a license for 3 machines.  If it needs to be installed on more than 3 machines, then consult Microsoft small business for price options.