I’m in the process of looking for a used car and I can tell you that this shopping process is horrible. It’s fraught with inconsistent experiences, scams, poor dealer contact, and far too many problems. I wrote a short rant on the Ping about this last month for background.

During this shopping process I needed to use multiple tools: cars.com, AutoTrader, Craigslist, car dealer sites, Google Docs, Google Maps, AutoCheck, CarFax, and the telephone. Come on - that’s ridiculous in 2010.

Here are the key deficiencies I can see.

Listings are spread across different sites. Sometimes there’s duplicate listings, sometimes not. cars.com rules the roost but AutoTrader has some, Craigslist has some more (including phishing listings) and there are other regional sites out there too. Some dealers also don’t list on any of the big names sites at all. I know that this may be a side effect of the markets, but I also think it sucks. There’s a real need here for intelligent understanding of these listings - quality rankings, personalization, and the like.
Many car dealer sites are in Flash. ie, they are lousy experiences. Sometimes drop-downs work. Sometimes they don’t. But I’m not sure why I need Flash just to view something that works fine in an HTML table.
Proximity is just another attribute. Oftentimes, one will want to see cars in a similar location. The tech just isn’t smart enough to treat this as anything more than another checkbox or another tickmark on a list. A mobile app for this (“show me all cars within 10 miles of my current location”) is just waiting to happen.
Feature-specific search pretty much doesn’t exist. You can search by year, make, model, and trim, but options within those trims? Good luck.
No integration with essential tools like Google Maps, AutoCheck/Carfax, and Kelley Blue Book. The latter two tools are 100% essential when buying a used car.

The way I see it the two main problems facing a site that would fix these issues are ownership and the thinking of the used car industry itself.

Ownership is a concern because if I’m cars.com, my business runs on listings. I don’t have an incentive to share that via an API or the like because the money is in selling listing ‘space’, keeping people on my site and showing them ads; there’s no money in making the data widely available. And some dealers still insist on not listing things on these larger sites for whatever reason and thus, users are subjected to generally mediocre experiences scattered across sites. This is an old style of thinking, clearly, but it also pays the bills.

Insofar as industry thinking goes, well, that’s easy: the stereotype is that dealers want you to come in the door so you can be upsold or doo-dads can be added on since there’s so much money on the table. There’s money in extended warranties, there’s money in financing, there’s money in floor mats. This is mostly true… but upselling on the web is pretty sophisticated nowadays.

I’m concerned that this type of site can only happen if there’s a dramatic shift in the way the industry works. I’d rather just scale back and say, “Instead of being pessimistic, let’s just fix this problem.” Because it’s a problem if you’re any kind of researcher when it comes to buying things - especially expensive things like cars. I can deal with lousy in-store experiences if the pre-store experience is better.

So who is best geared to fixing this issue? Let’s compare.

Google. Google has the skills and the cash. They succeed in almost every market they touch. They’ve done next to nothing in the car space, though, and I wonder if this is due to the locked-up data.
CarMax. Arguably the cleanest top-to-bottom used car retail organization despite their generally high prices. On the downside development of such a feature would likely be limited to CarMax’s own inventory and ultimately would be a super search for CarMax. It wouldn’t change the world.
AutoCheck/Carfax. It seems like adding a killer search feature that isn’t just a partnership is a natural here. They have a repository of information already.
Kayak. If they can do it for travel, why not used cars?
Unknown startup or person. Will it be you?

At this point in time I think the dealers are in the worst position to improve the experience, yet they’re an instrumental part of it: they sell the stuff. And auto manufacturers want to sell new cars first, certified second, and don’t care much about used cars… so they’re largely out as well.

It’s a tough problem but, honestly, I’d be happy if someone took a good stab at improving this painful process.