1) I want a progress bar to go from 0 to the top following the end of the time out which is random.
For a progress bar to work, you need to know the endpoint before the program starts. If the endpoint is random, a progress bar going from 0 to 100% makes no sense because you cannot know if the time elapsed so far is 1% or 50% of the total time, for example.
When I try to use a case true false to put a start button, I have errors in the code, instead of having 202103A0001 I have 202103AXXXX where XXXX are random numbers.
Obviously you are doing something wrong, but you have not attached any code. There are dozens of different ways to do it right, but millions of ways to do it wrong. We cannot guess what you are doing wrong unless you attach your VI.
Did you study the state machine templates and examples?