Hi,
I have plenty of experience with web robots (crawlers and scrapers).
### proposed solution
1. Craigslist offers a XML based API to post ads. I have worked with that some time ago.
Basically, the system offers guidance for you to determine the criteria to create the XML and post it.
We can also do bulk and scheduled posts.
2. The solution I offer is really flexible. It's a small php based server you can run on windows, linux or remote. It's up to you what is the best solution.
Please contact me if you have any question.
best regards,
Marcos.