George. Nicest kids I knew in college were George School grads.
Deerfield or St Paul’s?
St Pauls
Hill or Mercersburg
Hill. I know almost nothing about Mercersburg but Hill’s school song video on youtube really got me
NMH or Kent?
NMH. Icecream!
Putney or Colorado Rocky Mountain School?
Colorado Rocky Mountain School.
Andover or Exeter?
Exeter!
Cheshire Academy or Lincoln School?
Cheshire as it has 164 courses offered!
Loomis or Choate?
Loomis!
I’d have to go with Choate on that one (I’m applying to both plus Cheshire and Taft) but they are both my top choices! 
NMH or Groton?
NMH! They make their own ice cream!
Madeira or Foxcroft?
Milton.
Andover or Exeter?
Madeira for the location and Andover (although I’m not applying, way too hard for international students).
Loomis or Taft?
Loomis! I visited Taft and didn’t really like it
Exeter or St. Pauls
Exeter.
Groton or Loomis?
Loomis - new PHI!
Kent or SAS?
SAS, seems like such a nice and welcoming school
Exeter or Andover?
Andover. It’s weird because I feel like I’m more of an Exeter person but I liked the vibe at Andover more.
Choate or Deerfield?
There is only one correct answer and it is… CHOATE!
Canterbury or Pomfret?
Canterbury! I see their posts on my Instagram explore page all the time, seems like a very lively school.
Putney or The Webb Schools (CA)?
Putney!
Berkshire or Pomfret?