Can't connect two non-apple bluetooth headphones at the same time

I cannot find a way to get audio via two bluetooth headphones at the same time, because it seems that that is only possible if one of the headphones is made by apple. As far as I know, this is a restriction of the Bluetooth 5.0 capabilities by Apple... My 4 year old Samsung S8 could do that, as well as a lot (if not all) other Bluetooth 5.0 enabled devices of which I am aware.

For my 7 hour train ride this leaves me and my girlfriend two options of enjoying media together:

1) Big ipad screen with a USB C to Audio jack converter + Audio jack splitter + 2 wired headphones

2) Smaller Samsung phone screen with the same two headphones connected wirelessly.

I have it summarized in the pictures.

OR I purchase headphones made by apple or Beats (owned by apple).

Am I missing something?? I specifically checked that the ipad has 5.0 before buying it.