Amherst is the obvious choice here for your interests: liberal arts college, open curriculum, college town setting, great English department. It's a reach for everyone, but you're competitive from what you've told us so far.
I don't understand how you are a special case. Your ECs look fine to me. You have a lot of community service and a long history of competitive chess. I can't say if it will be "enough" for UVA, but considering you are in state and your stats are okay, you may as well apply early action.
I also don't get what you mean by "setting the bar low." UVA is one of the top ranked public schools in the country, and W&M is very highly ranked as well. You are lucky to live in a state with good in-state options.
This feels very reach-heavy to me. I'd say to pick 4 of the reaches, keep Cincinnati and OSU as safeties and Case as a match (but show interest). That would put you at 7 schools. I would suggest you add 2-3 more matches to give you more options if the reaches don't pan out.
I agree with @merc81 about Williams, Swarthmore, Carleton, and Dartmouth being some of the best fits based off your stated criteria. For matches, perhaps Bryn Mawr (if you are female), Skidmore, or Bard.
Personally, I hated most of the comments! "Add this column to the list of reasons Trump won," really? And I don't think the "helicopter parent" accusations are appropriate. It's not like she wrote their essays and actually did their applications. For kids who are applying to elite colleges, many parents at least look over essays and help manage deadlines. Mine didn't, but almost everyone else I know at my LAC had a good deal of guidance on their application from parents and/or counselors.
@HImom I agree that the liquidation of retirement assets is concerning, but I don't think that fewer visits would have appreciably increased their ability to pay for college. There's a huge difference between maybe $1000-2000 to visit schools and $240,000+ for four years at Claremont McKenna. It's true that many families wouldn't be able to afford either expense, but they're not comparable.
Also, keep in mind that the article is written about a mother of twins, so they visited about 12 schools for each kid. That's not crazy, especially since they did most of them while also spending time with family and friends in the area.