ISBoxer.com

Yeah i saw that and a few comments ago mentioned something about fixing it, mine looks like your second image

by config do you mean my ISBoxer toolkit profile?

yes, profile=config.
http://www.isboxer.com/wiki/Configuration_Sharing

https://pastebin.com/QTLQBTRT

The character set in focus is the DH 5x group (the one ive been testing it on)

OK, except for the fact the sync actions in the paste seem to have lost their mapped keys again, I can't see anything wrong (they're actually missing from the pastebin xml, rather than being an issue for when I paste back to the toolkit, so might be worth double checking your source profile)..

I just tested myself, and the load on character set option did work, but, only after I tried renaming and putting a popup on it, and when it still didn't work, I exited all games, and relaunched, and then it decided to work. I renamed back, and exited and reloaded again to test, and it still worked. So not sure why there seems to be a hiccup there with getting the first time to go, but it should work after a full exit and relaunch.

This weird thing happens where when i delete the entire key map and restart everything, when i next open up isboxer the old keymap exists with nothing inside it.

Reimported from your pastebin.

Been fiddling around with the character load keymap, its not working for anything. To test i did a text poppup and it just wont load until i hotkeyed it and pressed it. Don't know whats going on here.

Yes, there is something odd. I'm trying to replicate again so we can track down why. Once I renamed the load mapped key to Startup, and got it working, I can't break it again in that profile.

When I initially had the problem, the console outputs showed me that the Key Map being loaded, and the mapped key is queued for execution, but just doesn't appear to be executed (mainly as the popup I added didn't show up).
It is worth knowing that you can't use the character set load/reload mapped key for a partial character set. It must have the whole set active.

Other than that, I suspect something is bugged somewhere,

I just tried clearing ISBoxer after saving, granted ISBoxer itself didnt get to reset, but i quickly setup everything and tried after an innerspace export and nothing.

Should i try reinstalling ISBoxer? Burn the comp?

As a side note, i did just try adding the Load X... to the active key maps ...keymap. as a plus that works but this thing still perplexes me