I want to buy bitwig but share it with a friend.

Does anyone know if you can run it simultaneously on two machines?

 

When you intend a breach of contract anyway, why buying at all?
You won't be allowed to run the soft with two persons concurretly by the EULA. So you will be treated like if you are "pirating" the software.
So using a software intentionally against the EULA IS the same as pirating.
This makes no sense to me.

 

I know it's a breach, but i want the updates. The question is will bitwig not allow me to run it simultaneously or will they know and rescind my license?

 

Also by that logic what is the point of group buying samples and such?

 

Ok.
On the Bitwig homepage FAQ there is the answer: "
Q: On how many machines can I authorize Bitwig Studio?
A: You can install Bitwig Studio on up to three machines at a time.

So you won't run into problems if you and your friend use two or three machines at the same time.

None, it's a breach as well.
If there are a rules in the license agreement, one should be aware that the vendor may use measures to enforce them.
May they phone home with the DAW and check the IP of two machines running at the same time but always on different IPs, or may they check if their content is used according to the agreements.
As long as you are aware of that there is - most likely - no problem (blocking IPs, not publishing your music with sounds that can be identified)

Most vendors are quite relaxed if you use their stuff at home.
For instance THE FOUNDRY, the vendor of a 3D package, says they know by whom, where and when every single instance of their software is used. They don't do anything about it as long as you just use the soft privately. If you use it profesionally, they'll send a lawyer.