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I don't see a slam dunk problem, but: See if you can clean up the backside of the board with an old toothbrush and some isopropyl alcohol. There's a lot of flux residue on there which makes it hard to see the actual soldering work in your second picture. Some of the soldering of the wires onto...

Rubber duck debugging!

I found that I'd get solder to flow through to the other side much more reliably when I started using additional tacky flux - the rosin core isn't always enough. The correct amount of flux is "more"!

Have you tried hiding the copper layers when you're trying to edit your silkscreen?

What's your input voltage like? Voltage at the charge pump looks pretty low, should be closer to 9v on pins 1/8, that's pretty much connected directly to the +9v source. Low voltage from your supply? Bad zener diode (D3?)