I actually asked him about this and he said to just listen listen listen. Sometimes I pause when I hear him say something I want to know. Eventually certain words will stick out that he says a lot - look those up. For example he always says という風に or と言う - back in March all I knew was textbook talk so I didn’t understand.
Idk if you watch curedolly videos, but she talks about the top down approach (try to get a general understanding w/o looking things up) and the bottom up approach (stopping to learn everything 100% basically). The way teppei recommends is more of the top down approach - more input is good. Stopping all the time just takes away from the immersion. As you study other stuff and your listening improves you will start to understand more.
Until about May I was only listening to the beginner series too, but I took the leap at some point and slowly I’m understanding more and more of the regular series now.
Just the act of listening even if you are doing something else gives your brain the input it needs to do the work for you. Obviously the more comprehensible the input the better, but I think you need to set limits for how often you look things up. Maybe every few minutes if you want? Also listen to the same episodes multiple times and you will catch more too
Let me know how everything goes 
Thanks for the reply! I have been fortunate that my situation has allowed me to spend as much time on this as I’ve been able to.
It sounds like you have had a pretty interesting journey also - I’m glad WK has made it easier for you to progress with kanji too
I think the native content like youtubers and podcasts is really helpful for understanding real Japanese speech. If you have any parts of the day like driving I’ve found they are pretty useful for listening practice time
It really is tough when you have responsibilities but I think its super cool you are doing your best to continue the journey - it shows some true commitment to your goals
Here is my current breakdown - I’m on a leach break right now as I had about 250 apprentice and 700 guru a few weeks ago I had to whittle down.
Good luck with your goals too! I hope you get to go to Japan more often too
(once a year would be too good haha!)
The famous たく-さん cracked me up… It was a nice read though.