Chapter 4: Getting Started with Cobalt Strike

1. Yes. It is necessary to plan the attack because you may get only one shot in which you have the advantage of the element of surprise. You need to know exactly when you'll be attacking the server and carry on with the operation.
2. Cobalt Strike is not free, but you can download the trial version online. A little bit of Googling may help here.
3. Yes, you can. However, for that you need to change the port in the team server script. Furthermore, running two team servers on the same instance will have a listener's port conflict. This can be avoided by using different ports for listeners during setup.
4. You could be connecting to someone else's team server with your credentials. It's highly unlikely but possible that you're in an MITM attack phase.
5. The older version of Cobalt Strike required MSF, but new versions don...