On the list item page under the re-listing it says that re-listing an item is 14 days.

So if a user list a new item for 30 days, and clicks 1x re-list, that would add 14 more days after the initial listing, and if if clicks re-list 2x that would add 14 more days after the 1 relist of 14 days? Is this correct?

I would have thought the re-list would be the same as the initial listing time, in other words, initial item = 20 days, re-list 1x = 20 more days, re-list 2x = 20 more days. I need a little more info on this as I may want to make some changes in this area of the classifieds.

Yes, you can increase the auto re-listing days setup in the config.pl file under in this setup below

#######################################
# Number of days to Auto Relist classified ad for

$config{'relist'} = 14;

>I would have thought the re-list would be the same as the initial
>listing time, in other words, initial item = 20 days, re-list 1x =
>20 more days, re-list 2x = 20 more days. I need a little more info
>on this as I may want to make some changes in this area of the
>classifieds.

Only the auction software can do this.

If I change the number of days to re-list in the classifieds, would I also have to change the number days to store the pictures before auto delete, like with the auction?