In the early 90's, i learned assembly on DOS using the A86 assembler and the 
book Using Assembly Language by Allen Wyatt.  It was enlightening to use the 
D86 debugger to step through other code, including the code in the BIOS ROM.  
The IDA disassembler came in handy later on.

A86 & D86:

http://www.eji.com/a86/

IDA:

http://www.dcee.net/Files/Programm/Utils/

I agree that NASM would be a great choice to learn with, and i think DEBUG.COM 
is adequate for stepping through simple code.  Below are links to additional 
free reference material for ASM on DOS.

https://web.archive.org/web/20180127094538/http:/kipirvine.com/asm/debug/Debug_Tutorial.pdf

https://www.plantation-productions.com/Webster/www.artofasm.com/DOS/index.html

https://pacman128.github.io/pcasm/

https://www.seabios.org/Developer_links

http://bespin.org/~qz/pc-gpe/

Best regards,
-Ben

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