Beauty is in the eye of the beholder. Great question, but the responses are going to be centered on what does your son want. I can only speak to my son's experience, as the Ivy schedule was EXACTLY what he was looking for. It took us a while to get there...to really understand all the options. But once we got there it was a no doubter.
We actually had a former D1 mid-major coach (who was offering my son) ask about other schools he was seriously interested in. My son mentioned a couple Ivys and the coach went on a negative tirade about the Ivys...."only playing weekend games, not travelling as much, playing a short season, and cold weather". My wife, son and I were all thinking the same thing after he was done talking....that sounds FANTASTIC! Here's the bottom line deal, my son was a very good high school player and college player. He had enough self awareness to know he wasn't going to play in the MLB, and that engineering was his future. The Ivy school he selected gave him the opportunity to study what he loved and play a sport he loved for 4 years. It was perfect for him given his situation, and his major. I've had many conversations with many people on this topic over the years, and many feel the same way I do. The challenge is identifying the possibilities, understanding what you want, and getting into some of these schools. My son would do it all over again in a heartbeat.
As for your follow up question, I think that would be a foolish policy if I'm a coach. Your job is to bring in the best possible players every year...essentially replace the ones you recruited a year or two years ago. There are all kinds of reasons people pick their college....not everyone has the same thought process. If I thought a recruit was a good addition to my team, I'd be going after him. The player is the one who has to make that call. The coaches job is to give him that option. In some cases, I think it is futile or there is a history of recruits passing over a certain level to get a perceived better opportunity. Goosegg used Stanford as an example.....and I agree. If Stanford is calling, I'm most likely taking that opportunity over anything else. But that is the way I think....maybe not others who have a desire to stay in-state or close to home.
To tie this all together, I think there are a handful of players every year who are offered the opportunity to play top D1, mid-major D1, D1 Ivy and D1 Patriot baseball. They've got to figure out what is best for them. Congrats if your son is one of them and I wish him well on his decision. He's earned that opportunity to choose. In some cases it isn't an easy decision, but in our case it was easy.