Saw this in many other schools’ forums, but it doesn’t seem like there are any right now for Yale! (I looked through the few older versions I could find, but they’re pretty short and focused on the residential college system).
Every college has pros and cons, as no institution is perfect. Listing Yale’s pros and cons (Residential College system vs New Haven or taking 5 classes per semester) is rather meaningless unless you’ve been admitted to Yale and another college. And those threads have already been done. You can use the search button to find many of these threads: Yale vs. Princeton, Yale vs. Harvard, Yale vs. Stanford etc.
It’s all about FIT, FIT, FIT. Suggest that any admitted students attend admitted student days at the schools they are considering so that they can see the school from a new perspective (admitted student versus high school applicant). You need to walk around the school and feel the vibe. I push fit so much because I have known kids at great schools that they hated because it just was not them. Go to Bull Dog Days. If money is a consideration, contact the Admissions Office. There is money in some circumstances. Plus, except for travel there are few expenses because you stay with a student and eat in the dining halls.
1 Pro of Yale: It's not Harvard.
1 Con of Yale: It's not Harvard.
Decide which of those you agree with, and you’ll know if Yale is right for you.
This question only makes sense if you are comparing apples to apples. There are very few apples that deserve comparison with Yale, certainly not more than a baker’s dozen or so, and if you are choosing among or between any of them and Yale you can pretty much relax because all of your choices are excellent ones. Then, once you have relaxed, take a hard look at the money differences to you, because it’s not likely the advantages any of them has over any of the others is worth a lot of money.
After you get past that, Yale has the best, almost magical residential system, an overall intellectual tone that is very high, and is only really challenged by Chicago and Princeton among its peers, by far the greatest arts/performance culture and participation of any of its peers, a culture of respect between undergraduate students and faculty, and less of a dog-eat-dog competitive atmosphere than some other peers. Like all of its peers, but to an extent only matched by a couple of them, it’s a wealthy institution that supports a huge range of high-quality curricular and extra-curricular options for its amazing student body.
Its surrounding community is less interesting and attractive than that of some peers, although that tends to make on-campus life richer. Its math, engineering, and computer science communities are smaller and their faculties somewhat less close to the pinnacle of their fields than is true at some of its closest competitors, although only Stanford really has it all in all of those fields. You often see that observation extended to all STEM fields on CC, but it’s not justified. And I think a con of all of the HYPS colleges, and a few others, is that they seem to herd students into a limited number of career paths that offer high initial pay and prestige but low medium- and long-term satisfaction. The students arguably aren’t forced to hustle, and don’t take enough risks.
A final con: As one can note from @Hunt 's comment, it may be stuck on comparing itself to Harvard (and, to a slightly lesser extent, Princeton), when it should be paying more attention to Stanford (as Harvard certainly is).
Excellent summary @JHS. The only point I would quibble with slightly is the last one you made. With Yale’s president and college dean both being Stanford alums, I suspect the administration is well aware of Stanford as a competitor for top students.