Going to Stanford was one of the best decisions I have made. That said, my positive experiences were not necessarily due to the University's poilicies; rather, I had many of my positive experiences in spite of them.
Whether you should go to Stanford depends on what you want... Here are my observations:
Negative: Techie/fuzzy divide
You'll learn about this quickly at Stanford. Techies (engineering, natural sciences) and fuzzies (social science, humanities) have a very different experience with the school--there is respect between some of them, but often there isn't, and techies are treated as neurotic nerds, fuzzies as students who don't learn anything substantive. I myself was a "fucky" - double in international relations and symbolic systems (CS/Psych/Phil of Mind/Linguistics, and got a taste of both worlds.
The University's policies don't help here because techies and fuzzies are treated so differently...
If you are in a techie major, expect to pay a lot of money to get taught by TAs in huge classes. You will invest countless hours in your work for 3 units credit per class or you will fail. The curve is vicious enough you might just fail anyway. But if you teach yourself and survive the ordeal you will have a very marketable degree.
If you are in a fuzzy major, expect to have an intellectual orgy with small classes, great teaching, with little work required for 5 units of credit and an easy "A." Enjoy your college years and good luck finding a job; you'll need it.
Justifiably, most technical students feel cheated since they essentially pay to fund the humanities students... they DO have to work harder, so there's some truth to the idea they are the only ones on campus doing real work. I consider myself bright analytically, a former math nerd, and struggled to make A's in CS. I am a good but not brilliant writer and qualitative thinker. Earning A's in History and Psychology came with no real effort.
Unfortunately this dynamic often gets falsely carried over to the idea that those who go into humanities are not smart and don't work hard. I don't believe that at all... But for those who shortsightedly measure things by grades...
Positive: The students
Some of the most incredible people I have met, and the number one reason I would choose Stanford again if offered the choice. They are diverse in interests, outlook, and personality, and most defy the stereotype of the over-studious study rat. There's so many things one can get into... a cappella, social dance, Alternative Spring Break, Stanford Film society, language theme houses... and most end up pursuing many different things outside class. Deep, spontaneous philosophical discussions happen often; more often than is even good for grades. I think more than most of the Ivies, Stanford attracts the Renaissance wo/man. Stanford dtudents push their boundaries in many different directions, not just their career path.
Negative: Lack of support and guidance
That said, I honestly believe almost all these great things at Stanford are created with the time, talent, and yes even money of students. Most student groups receive 90% of their funding from special fees that students pay quarterly. The University has no good resources on campus for putting together events - the bookstore is way overpriced as is the food, and it doesn't help that "nearby" (~10 minutes by car) Palo Alto is even more expensive. Its students keep pushing for a student union as a social center for campus, but the University insists it does not have the money. (Note: It does have $100,000 it can invest in each Palm tree on the campus).
That doesn't stop Stanford from taking credit for its students' blood, sweat, and tears. I was a coordinator for the Alternative Spring Break program... One thing that infuriated me the most was that we had to write "Stanford Fund" leters to alumni donors telling them how their contribution helped our organization. It coughed up ~$2000 at the expense of our students' time which could have been used learning about the social issues of their trip. ASB's budget is ~$26,000. Just a note: we don't take service vacations; as should happen in any humble service, our students eat, travel, and lodge as cheaply as possible.
Negative: Palo Alto
A bunch of superficial, selfish, and unbelievably dull rich pricks. They are all-too-happy to enjoy Stanford's resources, but are student-unfriendly, shutting down the city at early hours so they can go to bed and complaining of noise from the University they chose to live next to (so we can't even use our own amphitheatre). Stanford makes Faustain bargains with Palo Alto, agreeing for example to build it an elementary school in exchange for PA's gracious allowance for Stanford to build on it's own land. I sleep better knowing my tuition helps poor oppressed Palo Altoans make their BMW payments.
Positive: Residential Education
The dorms are great and staff are well-trained to deal with students' emotional and psychological problems should they occur. There is a very open policy toward alcohol use, in the sense that RA's are treated as counselors, not police. The freshman dorm experience will make for one of the most fun years of your existence.
Negative: Administration and Bureaucracy
Inefficient, disorganized, unhelpful, and rude, though I don't think this is necessarily abnormal at a University. A warning: these people are there to safeguard Stanford's money and reputation... they will almost always prioritize it over the success and welfare of individual students. I have friends who have demonstrated to me this includes engaging in and covering up ethically questionable behavior.
Unfortunately these officials end up rolling back some of the positives at Stanford. Case in point is the alcohol policy, which is becoming more restrictive and authoritarian. Stanford is afraid of being sued.
The Stanford cops are really despicable. Not only will they treat you like the scum of the earth for running a stop sign... on a BICYCLE, but they go overboard in looking to give MIPs. This crusade to stop underage drinking included taking videocameras into the Exotic Erotic party where many students were scantily dressed, ostensibly to document underage drinking.
Positive: Opportunities available
The world is your oyster at Stanford. Whatever you want to do, it's there; if not, you can bring it to campus and find students who will share your interests. I honestly believe no University has so many strengths across the board. Just remember, it must be YOU that makes them happen. You'll find lifelong friends and faculty members who will make the project easier, better, and more enjoyable... the central University will in general only make your life harder.