When I started learning (even though it was just a few years ago) there were fewer tools available. JPDB was being actively developed at a fairly rapid pace back then with some promised features being ones I wanted to use. Unfortunately a lot of those features never came to fruition and the dev has essentially abandoned the project as it stands. Basically, these days I would mention JPDB as a tool to be aware of but there are better options. Bunpro’s vocab system now exists and the quality of beginner Anki decks has shot up massively as well.
JPDB does support importing and there is a janky exporting system of sorts so it is possible to use it as a tracker. This is probably the main reason I would suggest being aware of it as it currently stands. I actually did this for a short time, marking entire books and shows as known so I could see how many words I had come across. I didn’t find it that useful personally, especially as JPDB mostly has media I am not interested in in its database. Maybe others would find it useful though.
What I would suggest these days is to use Natively as a way to find easy or level appropriate material. The meta on what was easy when I started actually involved a bunch of stuff that is a step or two up from the super easy stuff (which Chimmsen is currently ploughing through speedily!). As Chimmsen uses Bunpro for vocab it may be a better suggestion to set up a custom deck for a show they wanna watch and then use that to track their coverage or slowly chip away at it in the background. If I personally were starting out again today I would just roughly follow the Natively difficulty rankings as Chimmsen is doing already though, so long as it is interesting.
As for listening, using Japanese subtitles definitely helps but if it isn’t an option then I’d say you just gotta bite the bullet and go for it. I do believe there should be some options for getting subtitles working if you search around (although it would likely involve moving to a service that isn’t Crunchyroll and using a VPN, etc).
Hope that info is helpful. Good luck and enjoy!
Edit: Just thought of something I did when starting out which may be of use for the listening dilemma. I used to watch a show with English subs first and then the next day or week I would watch it again with no subs. This meant I was already primed to catch things and it helped me start to connect the dots and pick out certain phrases. If you have the patience for it then I would recommend it.
I had no trouble finding things to read that are easy AND enjoyable 
In the beginning I didn’t know they existed or that I could deactivate them, so I accidentally created a bunch of them while dumping the N5 vocab in. It’s deactivated for now and in the future I will manually add some ghost for really troublesome vocab or for rare cases/nuances I always forget.
but either way, watching has become more enjoyable and I hope my ability is enough to still understand the plot when I catch up to the new episodes.