U-boot supports dual-booting, doesn't it?
So in that case I wouldn't see why anyone couldn't be able to boot 2 OSes if they wanted too, even from a single SD card.
In case U-Boot doesn't support it, the technical question to answer is, how does one get an ARM system to dual-boot properly?
I suppose someone could use either a modified U-Boot (which is silly), or just have U-Boot somehow boot into a GRUB menu via initramfs (GRUB can be compiled on ARM) with a menu to, well, dual-boot. I remember SolidRun doing a custom solution for CuBox-i with an installer, where they simply have a downloadable rootfs called Ignition with a menu of things you can install from the Internet (Ethernet or Wi-Fi) and overwrite the SDCard with your OS of choice. Maybe something like this for Pyra would be really nice.
Oh, here's a link to a video:
There is source code for it, though it only supports imx6:
https://github.com/SolidRun/ignition-imx6
Maybe if Pyra did have an installer, a dual-boot option should be included. Maybe instead of shipping Pyra with what are basically netinstall images, have them with Pyra OS by default, so you can just exit the installer and go to the default. Idk.