I want to take a dive in the deep and dark depths of the nspire and learn to do stuff with assembly. I figure the way to start would be to learn to work with ndless and C, but for assembly I have no clue where to start or even how.

I know it will take more time and I definitely need to go with C/C++ as well (I'm trying to learn it anyways), but assembly attracts me for some reason I like the low-levelness of it.
I'll start working through ARM tutorials then and see what I can figure out
[Edit: ] I guess the first thing I should do is update ndless from r685 to r825

I just found the same page and I'm reading through some others now. I can surely say this is going to be an interesting journey, wether I manage to last or not

As Lionel Debroux points it out, ARM assembly is not the recommended language to develop for Ndless, although it can be a good option for low-level interaction with the hardware of for performance (as for example used by Goplat or calc84maniac for their emulators).

So I haven't really been maintaining anything in the Ndless SDK to make things really easy when developping in ARM.
But I have fixed what has been broken in the past revisions for your two to be able to get your hands on ARM assembly. Don't except things to go without any hassle, but you can report anything missing that could help you.

1) Download the Ndless SDK r833 or higher
2) Have a look at _samples\helloworld-asm I've added
3) The Makefile template and the Ndless Editor are now ARM assembly aware. When creating a new project, build your .S (mind the upper case, so that the file is processed by the preprocessor) with Tools>Build to generate the Makefile as you would do for a C/C++ program.

Some things (defines, structures, ...) won't always be directly available in assembly, in these cases you'll have to browse into the include files to understand the C definitions and translate them into assembly. The  Hackspire Wiki will also be a good source of information.

@Extended thanks for the tips
As for the hard/problematic part, that's part of the reason why I want to do it. I like the idea of a challenge and venturing into somewhat unknown areas (though you guys most likely know more about it then I do atm). I'll do my best and see if I can come up with anything and if it all fails horribly then I'll go back to C/C++

The ARM instruction manuals (i've got the "technical reference manual" and "architecture reference manual") have lots of good information. Personally i love ARM assembly, i think it's a lot of fun and the instructions are really flexible. I never actually got anything to assemble for the NSpire, but i've played more with the GBA/DS anyway.

Well the DS has dedicated video hardware so it'd be hard, let alone sound.

I have a question though: When I comment out "bl lcd_ingray" in the asm example, the editor promptly closes (crashes ?). Commenting out "lcd_ingray()" in the C example however doesn't crash and the program works fine.

It seems that nspireio2 supports color screen buffers although the ReadMe doesn't advertised it, so skipping lcd_ingray() may not be a problem.
But the ARM demo does expect a gray screen buffer (2 pixels per byte).