First off, Hampshire has a very different educational structure from most other schools. There are no grades- instead, professors write evaluations of student progress at the end of the semester- usually one to three paragraphs' worth, detailing the work you've completed, your progress on course objectives, and the like. There are also no pre-planned concentrations or majors: every student is required to assemble a faculty committee and create his/her own program, with the committee's advice and approval. Progression towards graduation goes in 3 Divisions- Div I usually lasts the first 2 or 3 semesters, and simply requires that a student take 8 classes across the 5 schools of thought (we also have no departments- all classes are sorted only into "Cognitive Science," "Humanities, Arts and Cultural Studies," "Interdisciplinary Arts," "Natural Science," or "Social Science." This leads to a lot of great interdisciplinary classes, and many classes are even cross-listed over 2 or 3 schools.) and get to know the Hampshire system, with an assigned advisor. Sometime in the second year, a student begins Div II, which requires pulling together a committee of 2 or 3 faculty members and setting up a plan to complete 12 learning activities- usually classes, but also independent studies, internships, community service projects, and the like- anything that relates to the concentration you've designed and that your committee approves of. Div II usually lasts through the second and third years, and then comes Div III, which is a lot like a thesis- you assemble a committee, which may or may not include the same people as your Div II committee, and plan and carry out a very substantial year-long project. Div IIIs complete 2 learning activities- usually an upper-level class or seminar and a TAship. The Div III is almost the defining feature of the Hampshire education- it is a capstone of everything the student has done before.
Because Hampshire requires faculty committees for every student, student-faculty relationships are usually very good. Students have to get to know faculty well enough to know if they'll be able to work together, and, once they've entered Div II, need to meet with their committees to make sure that their education is proceeding in a way that makes sense. Professors have to know students well enough to be able to write an evaluation about them at the end of the semester, although some are quite guilty of relying very heavily on student self-evaluations. I've had great relationships with most of my professors, and usually take advantage of opportunities to go to office hours and talk about my final projects/papers- because we don't take tests, we usually do significant projects at the end of each class, often relating the class to our own concentration and interests, and these projects can sometimes require a lot of consultation. I've also taken quite a few 5 College classes, and find that I also spend a lot of time talking to 5 College professors, trying to tailor their class to my personal needs- something most of them aren't expecting, but something Hampshire professors encourage.
I've had really amazing classes with less than 10 students- classes where a reading assignment is given, and the class time is spent discussing it. These classes have really expanded my critical and analytical abilities, and probably encourage the level of discussion that spills outside of class- I've been known to linger over dinner for hours, debating gender theory or talking about history with my friends. Hampshire students are very intellectual, often pretentiously so, and love to talk about the things they're passionate about. When Hampshire students slack off, it's obvious, and there are definitely times when class discussion suffers for it. When the class is really into the topic, though, fascinating discussion can result, and most professors don't spend the whole class time lecturing- they want to hear what students have to say.
Without grades, there's no such thing as GPA or rank at Hampshire, and it makes the atmosphere delightfully non-competitive. Hampshire students rise and fall by their own willingness to do the work- if someone's doing "better" in a class than you, it's likely because you aren't really putting as much effort out. Hampshire professors tend to be pretty understanding about things like deadlines and attendance, and will almost never make you write a paper on something you don't want to write about- there is always a way to tailor an assignment so that you're actually interested in it. Because everyone is so busy doing their own thing, looking for something that they really love and want to do, the atmosphere is pretty supportive- I love hearing opinions from other disciplines on the topics I'm interested in.
Hampshire is definitely not for everyone, academically. You have to be pretty self-motivated: because Hampshire professors are often pretty lax on deadlines, you have to be able to force yourself to complete your work on time- people have failed out because they just aren't motivated to ever finish their final projects. You have to be willing to go out and get what you want- Hampshire is small and doesn't offer that many classes, and, because we hate prerequisites, it's very easy to get caught in a loop of very similar near-introductory classes. A Hampshire student has to be motivated enough to make his/her work for a class be at the right level, and most Hampshire students are going to have to design some sort of independent study. Div III is obviously also a very daunting task, and not for the weak of heart or will. Those skills- the skills in self-motivation and making the world work the way you want it to- are pretty useful in the Real World, I've been told. As for the actual topics you study at Hampshire- probably not. Most Hampshire students get pretty esoteric with their concentrations, which is great for Academia, less for "real jobs."