If you’re looking to bypass CAPTCHA to set up scalable Craigslist posting service, it is going to be an uphill battle. Most users looking to do this want to post in the free sections. That means that even if you’re able to set up scraping software that passes CAPTCHA, Craigslist has a lot more restrictions for free posts.
It is very possible to get your account banned and your posts removed. Using multiple accounts, a VPN service, and/or a manual posting service will increase your odds of success.
But is it worth all of the effort? Track how much time and money is put into this type of black hat marketing tactic. Often times it is better use an approved Craigslist posting software platform. It will cost more, but you’ll be able to get better reach and a lot more consistent marketing campaign.
If you’re simply having issues getting by the CAPTCHA for legitimate reasons, this post does a good job laying how to fix the issue.