As technically exciting as this is, i would probably just bring a burner laptop, installed with a a default Debian install on a properly initialized LUKS partit

As technically exciting as this is, i would probably just bring a burner laptop, installed with a a default Debian install on a properly initialized LUKS partition, and a weak password, and a USB drive with a Debian install. Once inside customs, i'd verify the SHA1 sum of the USB drive image vs. the one on the Debian site, and reinstall the machine, setup a VPN back home, and pull the data i need onto the machine. Repeat the "dummy" install when leaving the country.