New Order or New Billable Item?

I have existing users that I need to get setup with their monthly billing. I must have missed something because I figured setting up a billable item for them with my pre-configured service would work. It does not, it adds this to my view on the clients account but even though it is reoccurring it does not send an invoice on my scheduled date.

So my question is should I have setup a new order instead and will doing it this way add it to the clients account and bill them every month or is there something else I need to do to set this up for existing clients?

Also when I add this item to the account and add the domain that it goes to, it gets everything wrong. I thought that WHMCS was connected to the server? If that is the case why does it get the user name and the IP address wrong? I can understand that it will not get the password but the rest of this is clearly available on the server. What did I miss setting this up that WHMCS does not work with the information on the server?

Another thing that does not work setting this up as a new billable item is that I have prorate setup and I wanted to change the prorated amount on an account because the client actually owes for the full month. Even after changing the price when I save it, it reverts it back to the prorated price regardless of my attempt to over ride it.