RoM does not allow software boxing, they're all uppity about third party = automated scripting. link

"2) Is it illegal to use a program to send keystokes to all open windows by hitting one key, and *NOT* having it automated?"

Number 2 is a big no no because it uses a third party program.

Multi Clienting is allowed just not a scripted multi client.
So, you can hardware box and you can run multiple clients on one box, but you can't use anything like Keyclone to tie the accounts together.