Hi Shawn,
1) Welcome to Auctiva! In order to proceed through the checkout process yourself, you will need to post a test listing in category # 14111; perhaps a "Buy It Now" listing with a price of one penny.
Then, you will be able to log-in with another eBay username, purchase the item, and proceed through the checkout process. If you don't have a second eBay account, you may need to solicit the help of a friend or relative who also has an eBay account. If you offer check/money order as a payment method and select that option during checkout, you actually won't have to pay for the item.
We also have screen shots of the Auctiva Checkout process available, which can be accessed by clicking the "Checkout Settings" link under the "My Account" tab within your account, followed by the small "View Screen Shots" link on the ensuing page.
2) In order to create shipping discount rules for buyers who purchase more than one of your items simultaneously, you will need to set up "Shipping Discount Profiles", which can be done in the "Preferences" section of your eBay account. When you are creating your listings through Auctiva, as long as you check the box next to "Make this item eligible for a shipping discount according to my eBay preferences", the shipping discount options set forth in your eBay preferences will automatically be applied to your buyers who purchase more than one item.
I'm uncertain whether it is possible to set up shipping discount prfiles which will allow you to accomplish exactly what you are looking to, so I recommend fiddling with the options that are available there. If you have any additional questions regarding this specific issue, I recommend contacting eBay's customer support department.
I hope this information proves useful. If you have any further questions or concerns pertaining to your Auctiva account, please file a support request using the appropriate link on our help page:
http://www.auctiva.com/free-auction-software-help/help.aspx-Mike