Honestly, 36/52 isn't that much different from 34/50. I think I calculated that the 28 with a 34 is like a 27 with a 36 (that makes sense in my head, but probably doesn't make much sense written out).
And I never felt like I was ever "spinning out" on compact with an 11-28 cassette. I'd probably go back to compact if the opportunity arose. It's just that I bought the bike without a crank and the only option that Amazon had in stock for 2 day shipment at the time was mid compact. And that was what the bike originally came with. So I figured why not give it a shot?
I was thinking of trying Mt Greylock, and friends say you really want to have a compact there, and maybe even an 11-32 cassette. I need a long cage derailleur in the back for an 11-32, though, and DI2 derailleurs are not cheap enough for me to consider that.

Although, a friend did extend his derailleur hanger with a "wolf tooth", and that seems like a cheaper/better way to do it.
https://www.wolftoothcomponents.com/products/roadlink
I gave you a follow on Strava! It's hilly around central mass, but the Berkshires start getting "mountainy."

I'd love to give it a try sometime.