I would like to tackle a couple of your concerns: post college earnings and D1 athletics.
First, earnings. Among the many college ranking systems out there, Money magazine has one that is particularly interesting. True to there name, it is based on money - post college earnings relative to the cost of each college. All different types of colleges are lumped together in one list. Both Grinnell and Holy Cross are in the top 30%. Of the 750 colleges ranked, Holy Cross is #155, Grinnell is #205. This is consistent with your research.
What’s revealing is a second ranking that Money dies from which they generate a list of 50 “most transformative” colleges. To do this they evaluate the potential of each college’s freshman class by their admission’s profile and then compare it to later earnings, as reported by Payscale, to see if they overachieved or underachieved their predictions. Holy Cross ranked #15 on this list, Grinnell did not make the list. Money concludes that graduates of schools like Holy Cross realize excellent return on investment.
The second issue is athletics, which I consider a red herring in this decision. I’ll explain.
Holy Cross is a founding member of the Patriot League, which was formed by a group of academically excellent schools so that they could compete against like minded colleges. Sort of like the Iby League principles. It was founded 34 years ago as a non-scholarship conference. Its 6 charter members were Holy Cross, Colgate, Lafayette, Lehigh, Bucknell, and Davidson.
Since it’s founding, they have modified their position on scholarships and now allow scholarships in some sports but with restrictions. For example, D1 football schools are peritted 86 scholarships, but the Patriot League limits its members to 60 football scholarships. This is an academics first sports conference in which athletics are de emphasized. To the best of my knowledge, Holy Cross awards scholarships in only about a third of the sports they sponsor. (Check elsewhere fir current information.)
As a point of comparison, the Ivy League is a D1 sports conference. Would you turn down Harvard because it’s a D1 school?
Let’s talk about D3 schools. They compete hard in sports. They want to win. They recruit athletes. Recruited athletes are priority admits. Whether it’s a national merit winner, a top minority student, or a recruited athlete, all priority admits get the maximum available financial aid. (Not all students are offered the max.) It is not an “athletic scholarship” at a D3 school, but it’s still money taken from the pool of financial aid resources that could have gone to other needy students.
While both the Ivy League and the Patriot League are D1 and make some academic concessions in order to get the best athletes they can, they are not bringing in students who they think are not able to do the work. They may be at the lower range of the student body but they are still capable. This is no different than top priority legacies and children of big donors among others. These same practices are true in the Midwest Conference in which Grinnell competes.
Here is the impact if athletic recruiting at these 2 colleges. Grinnell has more than 600 varsity athletes (men & women) in a student body of 1700+, which is about 35%. Holy Cross (men & women) has about 850 varsity athletes in a student body of 3000+, or less than 28%.
I say that D1 sports is a red herring because athletic admits affect the admissions process and the available financial aid at every college, regardless of whether or not they offer official athletic scholarships. I say red herring also because Holy Crosses not a big time D1 school. It limits athletic scholarships and deemphasises intercollegiate sports.
Grinnell is a wonderful school and you should go there if it’s the right fit, the place where you can thrive. Holy Cross is also a wonderful school and you should go there only if it’s a place where you might have a better chance to succeed. Neither the number of National Merit winners or the number of D1 athletes should factorinto your decision.