Keep in mind 95% of their site is not the product they are trying to sell. It is in craigslist's best interest to keep users glued to their site. If someone takes 30 minutes to find a used bike instead of five then great. Maybe there is a chance the user get's bored of cruising bike listings or on one of their many trips to see the latest postings will click on the job section. Craigslist uses their massive user base on the free portion of their site as a significant competitive advantage over all other job posting sites. It is actually in their best interest to make it harder for users to find what they want. Craigslist is not in the business of people selling stuff to each other, they are in the business of attracting enough eyeballs for enough time to their site to click on enough job listings to keep their revenues flowing. They have absolutely no incentive to change or improve. I am pretty sure when they look at their revenues (the ultimate metric), it is actually doing pretty well.