"Does it really matter...." is an intellectually lazy argument. Yes it matters.
No it doesn't not for everything or even most things. You're over-thinking things and conflating the important with the unimportant, the big things with the little. Stop sweating the little things.
I used to get more worked up about things, like you apparently are, but then in late 2005, after 20 years together, my wife was diagnosed with a brain tumor and died, literally in my arms, just 7 weeks later. I heard her last breath, felt her last heartbeat and learned what the word "forever" means.
So, having my NYT or /. connection encrypted isn't really that important - my banking connection, yes, but I try to keep everything in perspective. The scenarios you've described lack some of that.
I'm not "intellectually lazy" I just know what is and is not important - for me anyway.
Also, entities like Google are not encrypting their connection to protect your privacy, it's to protect their revenue stream, so third-parties cannot skim ad/search information w/o paying Google for it.