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We use Carsforsale.com for this. They do a great job on the data feeds and inventory. They pull our inventory to our website and we've also used them with Dealix. Best part? The feeds are free on the Carsforsale.com side.
We use three or four different companies that have this capability depending on what all options that you are looking to do.
HomeNetInc does not have a website option but can do this feed for you and they are no longer associated with Craigslist postings.
HomeNet use to subcontract out through CarGiGi, they are the #1 Craigslist posting tool.
Carsforsale.com is SUPER CHEAP! That is a good thing, BTW. They can provide a web option and do these feeds and I believe that they charge 99.00/month.
EbizAutos has probably the best website option for the bang for your buck on this and also can do the feeds for you with ebay & craigslist integration.
Dealer.com has the most intensive CRM backend tool along with all the previous options but it can get pricey (its who we use cause all the tools though).
Hope this helps.
We use carsforsale and ebizautos. both work great to send pics and data to most sites.
Craigslist is just harder to do...extra steps..but that is a craigslist thing.