Answer to 1) is YES. You got it exactly right.
2) You will not win more than the number you want. (it can be more than one). AS places a bid on the first item. They must verify a loss before they will bid on the next. Bids can be missed for auctions ending very close together.
example: two auctions end 10 seconds apart, and your lead time is 7 seconds.
AS will bid on the first auction. They must wait till the end and then query eBay to check the status. Since your lead time is 7 seconds, that only gives AS 3 seconds to verify a loss before bidding on the second auction. That's cutting it very close, so you may get a 'Not in Time' on the second auction. Durring slow times it may work, but on Sunday evenings when response times are 20 seconds or more, AS will not have a chance to bid on the second. The best way to deal with this, (it still may not work) is to change your lead time on the second auction to something shorter. This will give AS more time to verify and bid.
In any case you should NEVER win more than the number you want.
Hope that helps.