For one, it seems to be impossible to load a dylib using DYLD_INSERT_LIBRARIES from any(?) location outside of the app's sandbox. It also seems to be impossible to copy a file into the app's directory or sandbox, as sshd doesn't have proper entitlements either.
I was able to bypass this via injecting the dylib via Substitute and launching the process with the args -avvv /var/mobile/Containers/Data/Application/<app_uuid>/Documents/Dump, which succeeded.
I wonder what other solutions could be found here