I maintain a small search engine that allows users to search for any file in my organization's servers. I'm primarily looking for a tool that will help me model user's search queries and user characteristics. Specifically clustering their queries into groups like searching for Documents, movies, or music, as well as what the client's OS is. Can Seldon do this easily for me, or is not the right program for the job, or even overkill?

It sounds like you basically want a form of document clustering. Seldon has integrated the Semantic Vectors https://code.google.com/p/semanticvectors/ project which can be used to do this or depending on your technical level to look directly at Semantic Vectors or toolkits such as gensim https://radimrehurek.com/gensim/

zakn, since you said you're still trying to figure out where hike.io stands in the internet of hiking, you should know there is an app called "Yonder" that focuses on high quality photos of the outdoors, submitted by members of the Yonder community (who are by design mostly hiking types). They have an iPhone app and have a UI modeled after Instagram. I've used it to find hikes around my area. You should check it out for the some of the social-oriented features it has.