You have a lot of great advice here. I agree that Bowdoin uses ED1 for hooked kids. My kid got in RD to Bowdoin. My two cents is have your son figure out if Bowdoin sings to him. If so decide if your admissions portfolio would look stronger with Sr year grades. If so apply RD and spend a lot of time on the essays. Also do the optional video. Bowdoin really wants to get to know your kid and see if he will be a good addition to their campus. My kid ended up elsewhere but it was a hard choice to make.
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Seconding the idea of picking a few EA/true safeties among Wheaton MA, St. Lawrence, St Olaf, Susquehanna, Drew, Clark, Muhlenberg, SUNY Geneseo - perhaps SUNY Albany (honors) for externship access. Macalester more of a target but a very good one for his interests.
Get them done now, send them, show basic interest, and focus on the rest. 
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This has all been really good advice. Thank you. We have not started paring down the list. The issue of so many “toss up” schools in the middle, or higher, suggests a more robust list is appropriate (although we are trying to target 20 applications or less). Based on the suggestions here, we will want to EA a few schools, including:
Hobart
Gettysburg
Union
Binghamton (SUNY)
Marist
And also have added Dickinson, Franklin & Marshall, and UCONN to the list.
We have a few non-LAC here, which are not going to be top of his list, of course. But he liked the visit to UCONN, and Marist is close to us. Thanks again!
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I also second the suggestion of Kenyon.
Thanks - there are several great midwestern options here, but we are really sticking to Northeastern Schools – Pennsylvania thru Maine. Geography is a very important consideration for our family.
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I, like many, think your targets are reaches for the most part, but I suspect you’ll have some choice at the end of it all. I would definitely add a few that are more likely to be a sure thing. Not only will that give you a little more certainty, it assures some choice if your top choices don’t work out for some reason. That’s often important psychologically. Those might include Dickinson and F&M, both of which share many attributes with the schools you like. (Especially the Maine schools.)
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Thanks - and agreed. As I noted in my update yesterday, we added Dickinson and F&M to the list. My eldest child, who is a rising sophomore at Bard, got into F&M with a nice merit bonus. I loved our visit there on admitted students day. But he fell in love with Bard and it’s been the right school for him so far!
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Bard is wonderful! I would have suggested it had you been looking for that vibe, but your list suggests not.
Fwiw, DS, who loved and attended a Maine school, fell hard for Dickinson at the admitted students day. He also really liked F&M.
Actually, lots of overlap with your list!
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Just my two cents, but there are certain colleges I think are sorta on the same branch of the bigger college family tree, such that they are often good recommendations to check out (of the form, “If you like X, you should perhaps check out Y”). And one of the great things about this community is we have so many people here who between them have explored almost all the notable branches, and are available to make such suggestions as relevant.
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Consider adding UVM to your likely list. My Wesleyan-bound kid loved it (and got in EA with top merit). It’s a smaller public school and has a SLAC-like vibe.
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Updated (Still-Too-Long) List, which takes into account the feedback received above. His academic rigor, in terms of available vs taken APs is definitely an area we are aware of. S25 loves history and environmental studies, and so that drives him to take related AP courses; but he understands that rigor in math and English is a potential issue—even if he scored a 35 Math, 35 English, and 36 Reading on the June ACT.
ED1: Bowdoin
ED2: Vassar/or/Colby/or/Middlebury
EA (all safeties)
Binghamton
Gettysburg
Hobart
Marist
Union
RD:
Reaches
Amherst
Colgate
Hamilton
Haverford
Wesleyan
Bates
Targets:
Connecticut College
Skidmore
Bucknell
Lafayette
Safeties:
Dickinson
F&M
UCONN
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You may be closing in on what I sometimes think of as the “get petty” stage. As in if you end up with too many colleges that are good fits for the really important stuff, you can then start striking them for less important stuff.
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If you would like to read a few brief comments on some of the colleges you have mentioned, this post may be of interest: NESCAC Spoken Here: - #5 by merc81 .
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Definitely too many schools, but good list. Very similar to my C25’s.
Serious question — putting aside fees and effort, is there another downside to more applications?
I do think the biggest issues are fees and not giving the applications that really matter your best possible effort. But there are other issues, like the psychological toll of getting a lot of unnecessary rejections.
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That makes sense. I do agree that too many apps can make you lose focus. And the mental toll of that, as well as rejections, certain suggest a more measured approach to the application process.
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You want to be in a position to make every application a good one, and that takes effort. You understand this.
But the other part is that you can enroll at only one school, so at some point, either before applying or after getting decisions, you’ll still need to pick just one. At some point, more just isn’t helpful.
I think your list is good. I’m also a believer in making sure that if early options don’t work out, there’s choice in April. While you have a few schools on the list that are outliers in terms of size or vibe, kids do evolve senior year and may want something different.
So yes, you can – and probably should – trim a bit, but this is coming together.
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UPDATE: After visiting Middlebury and Haverford last week, we are moving Middlebury to ED1. He’s even quasi-interested in the “Febs” admission. We are aware of the better Midd ED rates than Bowdoin, so we are moving Bowdoin to ED2 — we believe we will get a better shot at Middlebury ED1 than ED2; and Bowdoin is probably same low rates ED1 or ED2.
We also are removing Haverford, which he did not like. Similarly and for same reason removing Conn College. He also wanted to add Pomona as a reach because of a presentation given by Pomona during a “six college tour” earlier this year. Go figure.
And finally got “petty” and dropped F&M. So at least we’re down to 20 schools now. I could see us dropping a safety or two along the way, but currently he’s feeling risk-averse and would like to stick with the 7 he’s got.
ED1: Middlebury
ED2: Bowdoin
EA (all safeties)
Binghamton
Gettysburg
Hobart
Marist
Union
RD:
Reaches
Amherst
Colgate
Hamilton
Vassar
Colby
Pomona
Wesleyan
Bates
Targets:
Skidmore
Bucknell
Lafayette
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Progress!
I note if you have properly categorized your Likelies/Safeties, definitionally you really should not need more than 2-3 for risk management purposes.
That said, choice is nice! So if you are legitimately unsure which Likelies/Safeties you would choose if admitted, that is a perfectly good reason to do more.
I would keep an eye on the application work load, however. Which could involve as little as making it clear if he is in the middle of applying and starts feeling like he would rather concentrate on some of those Likelies/Safeties rather than others, that would be fine.
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