Start with local ones. Neighborhood, businesses, religious groups, your parents employers. The $500 - $1k ones. The big national ones - I suppose someone wins but no one I’ve ever seen.
Most money comes from the school itself. But not a school like Midd unless you have need.
If they recruited you, maybe a school with merit has as well ??
IMO outside scholarships are few and far between and mostly worth very little $$$. The exception is corporate scholarships for employees kids or ones that accompany a national award or competition. Our local scholarships max out at $1500/year. Nice to have but they don’t really make a dent. If you need merit then look at schools where you are likely to get some (not Midd.)
To your point one kid of mine got $2k one time. The other $1k. Both from my company.
One kid applied to many national ones. Second kid none as we realized that was pointless.
I have a friend who got a small local one for four years but need and a specific county of residence were a factor.
@NewYorker7 if you are willing, would love to hear what you eventually decided on, have a similar situation!