If you're generating every single possible password up to e.g. 8 characters the password's quality doesn't matter, only the length does.
I wouldn't consider an 8 char password secure, no matter what the entropy is.
But the most effective "rainbow table"-like table is a look-up table with the followings:
* leaked password in plaintext, associate with email and any ID (forum username??)
* hash all of those passwords without salt
* hashes (with salt) of known leaked passwords (you try pas$w0rd and found a match for some hash with salt) - this only works if your attack succeed.
If you do a quick count you won't be surprise most passwords are fairly short and simple. If two complex passwords appear to be very similar, you can assume with a good probability they are used by the same person. You can learn some private data from just looking at password (e.g. birthday, pet's name, door number, company they worked for, sport team they root for, which many turn out to be the crucial hint or actual answer to security questions.)
I have never opened or downloaded any leaked data and don't know if it legal for use at all, but the black market probably has over petabyte volume of such data available.
It would be very interesting to see the whole world attack couple hashes per day. Imagine you go to a website, it gives you some plaintext, and you run a couple quick scrypt with random salt, and return the response. Now with a billion online users, run this every day once, you may end up finding one successful match of "this password == this hash with this salt" once in a while. But hey, that's what botnet can do...and then bitcoin!
What you describe is not rare, can be done with cross-site scripting. How it happens depends on the injection method (perhaps SQL injection).