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Someone had posted an android app awhile back that just reads random numbers to help with comprehension, its called kikisuuji - japanese numbers if you want to give it a try.
I haven't seen one, but it sounds pretty useful.
This is by no means a flowchart, but here are some resources I've used here and there:
Genki CDs - Goes without saying, really. Listen to the audio for the lesson you are working on, do the listening comprehension pages, etc.
JapanesePod101 Listening Comprehension Playlists - These are short little videos that have some dialogue and then a question. They have videos for what they call absolute beginner, beginner, intermediate, and advanced. I've only really listened to a handful of them, so I can't attest for their usefulness, but it seems worth checking out.
My Kikitori - This website has 12 "lessons" of short dialogue and quizzes that follow. It starts from beginner and goes to what I suppose you could call lower intermediate, and has natural speed and slow speed audio for each dialogue.
jtest4you N5 N4 N3 N2 N1 - For listening practice specifically for the JLPT, you can find practice problems here.
Animelon.com - If you enjoy anime, you can watch with easily controllable and clickable subs on Animelon. A popular recommendation for easy listening is Shirokuma Cafe.
Podcasts - To get accustomed to the sounds of natural conversation, some people like to passively listen to podcasts. This means that you just let the podcast play, but you aren't actively trying to figure out what's being said. Also, of course, podcasts are great listening practice for non-beginners trying to get their hands dirty in native material. ひいきびいき is a podcast that I enjoy.
(Android app) Kikisuuji - This is an app I've used to practice listening to numbers. You can pick the number of digits for the number, dates, times, and days. (Unfortunately for dates, there is no option to have only month and day.)
There is a variety of free resources available online if you search Google for Japanese listening practice (+beginner, n5, etc). Poke around and see what you can find.
If you have an android device, here is a simple app I created to help with listening to numbers. https://play.google.com/store/apps/details?id=appinventor.ai_baclontz.Kikisuuji