So @websensation what is your answer?
Ha-ha, this is an interesting question.
During April of senior year, before my eldest got all the financial aid stuff squared away, I was so rooting for Harvey Mudd, which was only 2 hours away. He also got into Princeton, which I loved when we visited, but I knew it wasn’t the right fit. Instead, my son chose MIT (before his Corporate NM Scholarship amount came in), which was across the country-waah for this clingy mom!
It was a little dicey at the time, but the finances worked out beautifully and wow, he chose perfectly well! MIT turned out to be the best fit for him by far, and he had a fantastic experience there! Plus, he met his wife there, so yeah, no regrets. 
Middle son, OTOH, I really wish had chosen UCI over Penn, but he needed a gap year, so it wasn’t an option at the time.
Out of seven admitted college choices, my son and I were fortunate to concur on the same school, from academic and financial stand point.
Nope. No regrets. I’m content with the schools both kids ended up attending. It’s on them to bloom where they are planted.
Yes. ShawD chose an excellent large school rather than a small school that I thought she would have thrived at and where she was recruited by the president. She chose it in part because of the tremendous school spirit. However, if she had attended the school I preferred, she would probably not have ended up in the perfect profession.
She applied to school expecting to study biology. The large school had a nursing department whereas the smaller school did not. In orientation, ShawD met a girl who was studying nursing and she decided to switch. The larger school would not let her transfer in to nursing but instead required her to reapply as a freshman. As a result, she applied to several other schools, one of which admitted her into a 5 year BSN/MSN program. She worked very hard, graduated at age 23 as a nurse practitioner and loves her work doing primary care. Had she attended the smaller school, she probably would not have met a nursing student and might not have found a sympatico career choice so easily.
His mom and I were in love with W&M. He chose Wake Forest…It’s proven to be a great choice, about as perfect a fit as you’ll find (for him). We are HUGE Wake fans now and are delighted he made that choice.
I went to a small, Catholic women’s college very much against my mother’s wishes. My paternal grandmother exerted huge pressure, really major huge, because her family had attended Vanderbilt including medicsl school for several generations.
Amazing how the pressure faded and even evaporated about the school and my major when I was a free ride by sophomore year. Then the pressure was lut on my sister to transfer there. Grrrrrrrrrrrrr! Ultimately, the child has to attend the school that is the best fit in many directions for him or herself. Disappointed parents, grandparents, and anyone else can attend their dream schools. It is, however, very reasonable to include cost in the decision. For example, I would have had to content myself with a post card of my dream school (cost equivalent plus to Yale) if cost could not be managed.
As a parent my only wish would have been that he could afford the school he wanted to attend. It just turned out to be too rich for us. He would have been surrounded by students more his GPA level. His current school offered him enough aid so we could afford to send him.
I was never concerned he would pick a school that was acceptable to us as parents. I just wish he could have gone where he would have liked to have gone.
Such is life. He will need to deal with many of these things in life. If it helps to cry it out, then go ahead.
From the list of schools D chose to apply to, she wound up at the best one she got into and the one we’d hope she’d pick (UC Berkeley). It’s been a challenge, but she’s built for it, and it’s super great for her major. Also, it’s only an hour away 
For purely selfish reasons, I wanted her to choose UVM. We both loved the campus tour, and it had some programs and features that really appealed to her. She ended up choosing the school that was really the most perfect fit – she loves it there. But I would really prefer to be driving her back to Burlington in August, rather than Worcester. I was hoping for visits that could turn into mini-vacations up there on Lake Champlain. Worcester… not so much. The upside is that it’s less than 90 minutes from home.
No regrets. #1 had several excellent alternatives and chose the one I thought was best suited for his academic interests (quality of overall program) and non-academic interests (big city): UChicago. #2 also had several excellent alternatives but chose the one that best met her core interests (stand-alone art school, in a real city in the East): RISD.
Both cost about the same amount (we were full-pay).
They each had very good alternative acceptances. It’s just possible that an important reason we were happy with the outcome is that we made very sure that their final list gave them good choices, good alternatives. IOW, we carefully guided them in constructing their lists, so that any of the schools they applied to would be excellent alternatives.
Our S had to choose from some really great schools. His pick has turned out to be over the top perfect for him. We could not be happier. He is thriving.
I wish my son had put more effort (as in visiting and interviewing and contacting professors) at Haverford. He was waitlisted there, but I think he would have gotten in if he had actually met the people in the admissions office. And I think it would have been a much better fit than Oberlin. But Oberlin is still a good school, and there is a reason why he is there. It has been a growing experience, to be sure!
My kids haven’t started yet, so it remains to be seen whether they made the best choices. My artist-writer-actor-singer daughter, who seemed destined for an LAC, surprisingly ended up in an intense business-focused program at a fairly large urban university. I have some concerns, but she is very enthusiastic about it. My non-artsy son, who really wanted a bustling urban campus, ended up at an LAC with an artsy reputation. I hope it is not too artsy for his comfort level. Like @MassDaD68 , I wish we could have afforded the college our son most wanted to attend of those he was accepted to, but I don’t doubt he will have a good experience where he landed.
I was pushing for UC Santa Barbara, but that was because the weather was incredible and I looked forward to visiting. Kids went for the East Coast…
@planner03 I don’t have my own answer yet because my kid took a gap year to study one language abroad before his start of freshman year at Stanford this September. But I sort of wished he would have enjoyed a slower pace and less competitive environment of Honors College on merits money. I hope my kid decides to just go into work force after undergraduate. I think Stanford was the right choice for him because he wanted to stay in the West coast to work and avoid cold winters.
My mother secretly thought I was making a mistake by going to Harvard. She thought I would be unhappy because it would be too competitive and I wouldn’t get into the performing arts ensembles I wanted. She might have been right about how that would have affected my happiness, but as it turned out, I DID get into many, and I was extremely happy.
@websensation My S will also be at Stanford this fall. I have a nagging feeling that it wasn’t the best choice, but time will tell.
@exlibris97 - “I was pushing for UC Santa Barbara, but that was because the weather was incredible and I looked forward to visiting. Kids went for the East Coast…”
I’ve lived in CA for 18 years, 5 of those years in Santa Barbara. Initially, of course, everyone falls in love with its perennial great weather, those beautiful beaches and, if you’re into parties, the school’s party culture, although I get the impression that its party culture has changed somewhat over the years. But you get bored with the same weather, the same beauty, the same parties, the same everything else. I felt so suffocated after a few years in S.B. that I went up north to the Bay Area where I was able to breathe!
After having also lived in the East Coast, the Midwest, the Southwest and now in a totally different region, I really appreciate the impact of the geographical diversity has had in my life. For that reason, my son’s college applications were heavily favoring the East Coast schools with two CA schools as backup choices. Your kids made the right decision. I’m generally in favor of kids going to schools that offer quite new perspectives and cultures from those they were born into and grew up taking for granted. For those kids who were born and raised in the East Coast, CA is a highly attractive destination, and vice versa. Of course, each kid is different with different needs, desires and dreams, hence my emphasis on “generally in favor of”…
I lived and stayed at lengths in many places: island, Vancouver, East coast, West coast and abroad. And I still prefer CA weather near the coast. You will get sick of anything. Hawaii whether, you can get sick of because it’s one season year around and geographically, it’s very small. At least in Southern CA, it’s two seasons. My kid already met many kids from many states and countries, and I am sure Stanford has lots of kids from other states. IMO it’s best to go to a college where you would like to live and work as long as the colleges are affordable to you and have strong programs across the board in case you change your major. My kid didn’t even apply to any school in the East coast. My kid and I have zero regret about not applying to East coast school. My only regret is our kid didn’t consider more seriously LAC and Honors College with merit money. To be honest, I have no idea if Stanford is THE best fit for him, but I am confident that it is pretty good fit for him. The only top East coast schools which remotely interested our kid were Yale and Georgetown.