The outdoor setting sounds incredible, I'd die for a rooftop terrace concert or mini amphitheater for a concert.
As for the songs:
Human
Simple and Sweet (The Cove City version)
Couple's Retreat
Overwhelming
Kid Again
Guillotine
Cautionary Tales
The Internet
Good Things Fall Apart
2 Rocking Chairs
Ooh
The last one's hard, but maybe Paper Planes to end it?
The order could definitely be fine-tuned, and a lot of these are relationship-focused songs, but it is what it is. I'm a sucker for romantic Jon. I think there's a solid balance between nostalgic songs that didn't hit the same numbers as some of his popular songs, and the songs that everyone knows.

Without a doubt,
"When you working out, and I'm just watching how your legs move
They would think that you was, like, developed in a test tube" AW YEAH