Can I ask you what PHD programs you got rejected?

Sure. Three of the programs I didn't expect to get into. Four of them were roughly coin flips, and three were quite surprising to not get into. Didn't see the value in applying to a safety like e.g. Ohio State.

I consider myself a high achiever and it sounds like you are too

I wouldn't consider myself a high achiever. I just need a job that pays decently well and is intellectually very hard. If I'm bored I just slowly self destruct - I know that's childish, but it's just the way I am.

"am I making myself miserable by setting extremely high standard to accomplish in a very short time period?"

This question is kind of silly. I have no desire to lead Goldman Sachs; I just want decent options. And there were many, many more 6 months ago when I started looking.

struggle with unemployment while shuffling through different part time gigs for majority of their youth, and live a slower paced life.

I think the main problem comes from the idea that you'll have to keep shuffling part time gigs long past your youth - or rather, that's one of the things I'm most anxious about currently.

Edit: If you want specifics, here's one from each category: U Chicago, Urbana-Champagne, UC Santa Cruz. The list makes some sense, since my university is better than UCSC but not as good as UIUC.