I do love solutions that involve supercaps

Maybe it would be better to use a relay instead of the blocking diode.
Have it energize when mains voltage is present and switch the DC output onto the cap.
This way you get zero voltage drop and it will still isolate the caps when the device is unplugged.
You might get better results with a few more smaller supercaps in series.
Just because of the higher output voltage and the boost reg dropout voltage being a smaller percentage of the total cap capacity.
Better design a professional looking case into the final version before it gets anywhere near a US airport

They love to panic at stuff that's unusual.