???How many times do I need to listen to the same content item????
I feel that in learning a language it is very important to have as much contact as possible with the new language. Ideally you should try to listen or read or review or write or speak every day. The more you enjoy what you are doing, the more likely you are to do it regularly. So, rule number one is ???do what you like to do???, at least that is what I do.
In my experience it is beneficial to listen to content more than once. The first time you may be trying hard to understand the content. You will probably save some words and phrases. The second and third time you are better able to focus on these new words and phrases. Hopefully you have reviewed these words and phrases and said them out loud a few times. When you hear them again in context this helps to reinforce your memory of them. You are also participating in a familiar environment in another language. This helps train your ability in the language. But if you find it boring or annoying to listen to an item, by all means move on to the next item. I certainly do. I do not like listening to boring content. It is a little like reading grammar rules. It does not really stay with me.
As a beginner I find that I have to listen to the same content five or ten times before I can move on to new content. When I am better at the language I may listen as little as twice or three times and then move on. If you really do not like a content item, do not listen again. Find something you like. In any case you can always go back to earlier items and try again or just to review and reinforce.
You will find it easier to listen again if the voice is pleasant to your ears. Spend more time on content that you like. There are some content items in various foreign languages that I have listened to 20 or more times. I always enjoy them. Some items I can only listen to once or twice.
So there are no hard and fast rules. Repetition is important. Enjoying yourself is important. Being in daily contact with the language is important. The decision is up to you. See what works best for you. And let me know what you think.