I wouldn't spend time dynamically shuffling the order. Just log the "hits", and generate a new program every hour/week/month/whatever. Write the script like this: 
while (<>) {
    s!http://www.theirsite.com/\W!http://our.server1/theirsite/\n!i   
+ ||
    s!http://www.theirsite.com/!http://our.server1/theirsite/|i ||
    s!http://www.dummy.com/\W!http://our.server2/dummy/\n!i ||
    ...
    logme ($&)
}

[download]
with logme an efficient log function. (And for those who want to complain about $&, think before you post).

Abigail

In reply to Re: Organising lots of simple regexes by Abigail-II
in thread Organising lots of simple regexes by ViceRaid

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