It all depends.
Gmail is the main email provider that does POP3 so you can forward all of the accounts to outlook. In essence if you have a few thousand, you have them all forward to ONE outlook account; then you go on your merry way posting ads and whatnot each with a different e-mail account and the confirm e-mails come to one account so you can activate the ads easily.
Some people need to be able to post more than one ad a day to CL or other places like that. A hundred accounts turns into a thousand, and then a couple thousand.
It's all above board...