Wow.... I remember writing 8086 assembly on MASM and another assembler I've forgotten the name of, and then also doing inline ASM in Turbo C++

The segment thing and the convoluted different pointer math caused real gymnastics if you ever had data bigger than 64k... such as images.

I always thought of the segments as windows of 64k but moving between those windows, esp with the limited register set, required some real mental gymnastics.