Auto posting or manual posting for craigslist?

I frequently face this question whether it is a wise decision to use an auto-poster software for posting ads on craigs list.
Well, the auto-posting software will save your time a lot particularly it it has CAPTCHA recognition module. But a software can't solve all the issues related with craigslist posting. You must have enough knowledge of how craig's spam filter works and what the category specific restrictions on craigslist to get success. For example, if you try to use an image while posting in jobs section, no software will help you. Because, image is simply forbidden in jobs section (although it's not mentioned anywhere on craiglist).
Another great issue is IP address. You have to find out an way to change IP address while using the auto-poster. This may be built-in feature of the software or may be done using another program. Remember no software can change IP address itself unless you have a source of different IPs (dynamic IPs). If you are using free web proxies to change IP, auto-poster is of no help for you.
Another point is that setting up everything on an auto-poster initially take significant time. So it will not save your time unless you continue for long time.

On the other hand, advantages are that with auto-posting software you may post at perfect scheduled time & immediate reposting may be done if the ad is flagged by the visitors.

In general use of auto-posters is not suggested and it is against TOS of craigslist.

How to avoid flagging on craigslist

Flagging is a wide controversial feature of craigslist.org.

Following are some tips to reduce flagging by the visitors:

• Make the ads non-commercial looking
• Make the ads local looking
• Choose the appropriate category. Don't post to non-related sections.
  
• Use as many different titles as possible. Titles should match with the theme of the respective category.
  
• Use as many different descriptions as possible.
• Avoid using a particular word or phrase in the titles and descriptions. So avoid using your telephone number, website address, email address or company name in each and every posts. Make some variations in this regard. In one posting you can use telephone number, in another posting you can use website address etc...
• If you want to receive emails from the visitors use craigslsit's anonymous email feature.
• If you see a sudden increase in flagging then take a hold on posting for few days and restart again.
  
• Read this Unofficial craigslsit Flag FAQ carefully. It will help you greatly to understand why your ads are getting flagged by the visitors.
  
• Post your question regarding flagging problem in craigslsit flag help forum. You can also contact craigslsit's support directly if you feel that your ads are being flagged while you are obeying craigslist's TOS. Here is the contact form.
• Finally, don't post too many. Leave some room for other posters.