I want to buy the Craigslist pro app and when I sign into iTItem as described and fast shipping! Aunes with my Apple ID and password ( both of which I know) it then asks security questions that I never chose ( or are even options to chose) in my profile.

If you don't know their answers then if you have a rescue email address (which is not the same thing as an alternate email address) set up on your account then the steps half-way down this page should let you reset them : http://support.apple.com/kb/HT5312

If you don't have a rescue email address (you won't be able to add one until you can answer 2 of your questions) then you will need to contact iTunes Support / Apple to get the questions reset.

Contacting Apple about account security : http://support.apple.com/kb/HT5699

When they've been reset (and if you don't already have a rescue email address) you can then use the steps half-way down the HT5312 link above to add a rescue email address for potential future use

There have been the occasional post from other people being asked for the answers to their questions despite it not being their first purchase on that device or computer.

To contact Apple about security issues you should be able to use link/number for the country where you and your iTunes account are from the HT5699 page that I linked to - you shouldn't be charged for that. Is that where you are getting that number ?