Love this thread idea!
I don’t know how much detail you’d like regarding the items, but I can maybe add some limited information for some.
004 - These are called patchins. There are a ton of these, but I’m not sure if it’d be easy to track down a particular release date for these. I guess these were made by Media Factory, based on the first patchin pack I found when searching the term? Not sure if another company took over or came before them>
Example pack:
005 - Created by Bandai, probably in 1998 (see image below). These came out of a gachapon machine. Here is the whole sticker sheet that the Starmie came from, and the little “seal book” that the sheet could be found in. The title of the item can be roughly translated into “New Pokemon Big Encyclopedia” or “New Pokemon Big Pokedex.”
There is actually an earlier released version, likely around 1997? The seal books are labeled as 1995, but similar to the Topsun controversy, they were likely not released in 1995. I actually have a single Starmie sitting at Buyee for the earlier version, but the sticker isn’t complete (the border is missing). The earlier version has the Red/Green sprite of the pokemon on the back. I can take a better picture of it when I have it in hand.
010 - Looks like it came from a SV minitin? Probably shouldn’t be too hard to track down which minitin.
013 - I think these have generally been called GB Pocket cards or GBA Card Collection or something? There are a lot of different variations of these small cards/minisquares though, so I don’t know which set this particular one belongs to. I also tried to look at some boxes available on Mercari, and it doesn’t seem to be clear what company produces them. (Nevermind, I found an article talking about them—there’s more information here)
014 - I think this is just a Korean pan/bread seal/sticker. I have a Hoppip one sitting at Buyee too 
Not sure what company or what year it was produced.
015 - I only know these are some lenticular produced by Meiji.
016 - The translation for the item looks like it’s called “Big Sticker.” Company is Nagatanien. Maybe you can find some more information that way?
018 - You can find more information about the set here. The site linked here is run by @nidokingdom, who is just generally very knowledgeable about these vintage Pokemon items (I know he knows what a few others you have here should be). He can probably help identify a good amount.
019 - Some more information from the stickerpedia.
021 - Think these are sealdass cards/stickers by Bandai. I don’t much about sets for these, and I guess the year is at the bottom.