It wasn't until I created a sinple 8086 emulator where you take the raw machine code instructions and translate those into not only the assembly instructions but actually emulate what those instructions do that I finally felt like I REALLY knew assembly.
My suggestion to others that want to learn assembly is to skip any assembly books. Using whatever language you want first start with a translator from machine code into assembly instructions, and then do an emulator. You only need to implement a small subset of the instructions, check out godbolt and translate some simple programs to know which instructions you need to implement.
Other than that all you really need is the 8086 manual, it has all the information there. I also found this site useful when implementing the flags https://yassinebridi.github.io/asm-docs/8086_instruction_set.... This takes less time than finishing a book and you learn a LOT more.
The goal is not to program in assembly at all but to truely understand the cost of everything and what you can expect from your hardware.