The challenge
"A multidisciplinary team representing business, engineering, and design roles is working on the redesign of the shopping experience of www.craigslist.com. The goal is to position Craigslist as a classified ads platform for students. You are the dedicated Design Researcher on this project.
"Use your research skills to provide the design team with research insights that help them to redesign the shopping experience (searching and buying) of Craigslist for the intended target group. Prepare a presentation to communicate your research findings and their implications to the team."
I summarized this: How might we position Craigslist as a marketplace for students?
Research questions
After defining the problem, I considered the specific research questions I had. These were related to students' current usage of Craigslist, their degree of satisfaction with it, and what tools they chose to use in place of Craigslist.
Usage
Are students currently using Craigslist?
How often?
For what type of buying/selling?
Why do they choose to use it or not?
Satisfaction
What do students like about Craigslist?
What pain points do they have?
Competition
What other tools do students use for buying/selling?
Why do they choose to use other tools?
What capabilities are they missing from Craigslist?
Method
Recruitment
I sent an email invitation to a mailing list associated with the University of Michigan School of Information. I requested student participants, as this was the only restriction defined.
Process
I spoke with participants via Hangouts or Skype for around 20 minutes each. I planned short discussions in order to speak to more people in less time (and also because I could not offer any incentives).
Participants
5 students, 1 recent graduate
Aged 20-38
4 female, 2 male
Overview of interview questions
How many times have you used Craigslist to sell something in the past three months?
How many times have you used Craigslist to shop for something in the past three months?
Did you have any frustrations using Craigslist?
Did you use other platforms for selling or buying in the past three months? 
Why did you choose that platform?
Why types of items where you buying/selling?
What would it take to make Craigslist your go-to marketplace?
My affinity diagram
Affinity diagram
To synthesize the data I collected in my interviews, I used an affinity diagram. I broke down my notes into individual chunks of data, which I wrote on cards. I then stuck these cards on the wall and moved them into groups of similar messages. Each group received a label describing its point. I developed the group labels into my insights.
Insights
It doesn't feel trustworthy
As one participant commented, "Everything about the design [of Craigslist] shouts 'Don't trust this website!'" Multiple users cited trust as a reason for choosing a different platform for buying and selling.

Evidence
U01 and U03 said that many sellers are not reliable and there is too much spam.
U01 and U06 said that for Craigslist to be their primary platform it would need to be much more reliable.
U01, U04, and U06 said they preferred other platforms because they reached a more trustworthy audience.

Recommendations
➜ Implement policies to protect buyers and sellers.
➜ Update the site's visual design to reflect its security, e.g. through transparency around the new policies and/or security certifications.
Screenshot from a student Facebook marketplace
I want to deal with other students
One of students' main reasons for using other platforms was a preference for dealing with other people affiliated with the same university.

Evidence
U01 and U04 preferred to use a student-only Facebook group for buying and selling.
U06 preferred a university-affiliated mailing lists because the audience is more trustworthy.

Recommendations
➜ Provide some means of verifying users' identities.
➜ Explore ways to associate user accounts or ads with universities.
➜ Consider creating university-specific sites.
It's good for local stuff
When students do use Craigslist, it's usually for items that are more likely to be exchanged locally.

Evidence
The most common types of items student bought and sold were:

Furniture – It's too costly to ship.
Books – Course reading often remains the same.
Event tickets – Especially for college sports.

Recommendations
➜ Explore further strengthening the local advantage.
➜ Explore different ways to make these categories of items more accessible to the student community, e.g. adding a student section that aggregates certain items or adding relevant filters within existing sections.
The features don't compare to other tools
Another big reason people chose to use other platforms is simply that they are easier to use. The main issue with Craigslist users mentioned was the lack of filters.

Evidence
U01 and U04 said other tools have much better filters.
U03 said he had trouble finding what he was looking for.
U01 said Facebook groups are easier to use.
U05 said eBay is much more usable.

Recommendations
➜ Add carefully considered and tested features, especially focusing on filtering capabilities.
➜ Update the visual design to inspire more confidence in users.
➜ As noted above, explore location-based features, user verification, and organization affiliation possibilities.
Summary
Although students definitely see shortcomings with Craigslist, they do use it – especially for buying and selling items that are locally relevant, like course books and event tickets. They also use Craigslist for large items like furniture that would be a pain to ship.
Currently, many students prefer tools like Facebook groups and mailing lists for buying and selling in their community. The main reason cited is greater trustworthiness.
The key areas Craigslist needs to improve in order to become a primary marketplace for students are:
➜ Provide visible security for buyers and sellers.
➜ Make the items that are interesting to students easier to find.
➜ Capitalize on its strength as a local marketplace.
➜ Modernize features and usability, for instance in filtering.
Discussion
There are a few factors that should be taken into account when considering these insights. First of all, "students" is a rather broad and diverse category, so input from six people does not provide a complete understanding of the target group. Moreover, all of the students were from the same university, and more females than males participated.
Further work
If I were continuing to work with this question, I would recommend the following activities.

More user research
Specify the target audience in more detail (students with what characteristics?)
Conduct more in-depth interviews.
Define target personas or Jobs-to-Be-Done.

Competitive analysis
Analyze functionality of alternative platforms like eBay and Facebook groups.

Usability testing
Explore possible new features (additional filtering, verification, university affiliation, etc.).
Prototype and test with target audience.

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