@Kyle Gospo after further testing, on the 06/30 image, if I connect via USB-C directly to a monitor, the display out works properly. Using any USB-C to HDMI dongle or dock, it does not.
i use a yubikey myself. but yeah, there's no ability to have an on-screen keyboard for the password unlock for luks. they tried a project in the past, but it didn't pan out.