Hi,
You can simply add some variables to the process (unless you have some facts in your knowledge session that you can access within the process) and initialise them according to the state you are in, then use exclusive gateways by checking their values and acting accordingly.
For example in your case add a boolean variable to your process i.e. emailWorkDone, with initial value false. Then if the 2nd path is started and completed based on your business logic then you can make the variable true and by adding a gateway between each timer and sendemail you can decide whether to send another email, by checking the variable, or go to the human task or something else....