The Initialize Array function will give you the same value for all elements. This is documented in the Help. Thus, you cannot use it this way. You can simply use two loops so you generate a random number for each element of your 2D array. I don't understand what you're saying about the Number to Boolean Array, or why you would even use that. If you use the 2-loop approach all you need to do is decide what you consider a "1". For example, you could say that anything greater than 0.5 is a "1". This can be done with a simple Greater? function. Note that this should be done inside the loop.
An alternative is to use the Continuous Random function to get an array of random numbers which you can reshape into a 2D array. You would need to decide if the distribution provided by that function is "random enough".
Are you trying to create some sort of random communication signal?
