Personally I enjoyed writing assembly with segments. You can have 64k of code, 64k of data and 64k of stack without trying. So long as no individual data structure is larger than 64k there is no essential difficulty working with 16 bit pointers.
When I think back I think it would be fun to have a hierarchical structure where composite data structures (think an array or hash map) are referred to with a pointer that goes into the segment register and you index inside a data structure with a regular pointer.
Lots of 8086 code was written that way. You’d use the segment register on paragraph alignment and basically take advantage of the << 4 + logic.
This code was a nightmare to port to protected mode 80286 so it went away by the Windows 3.1 era.
I went from a 6809-based Color Computer 3 circa 1987 to a 80286. I am kicking myself today because my Uncle Bob told me the job that paid me $1,200 to get a new machine created upwards of $60,000 of value so I could have asked for enough to get a 386!
I was told not to waste any time with 80286 protected mode by all the experts I talked to. I can't complain a lot because that 80286 was crazy fast. Fast enough that when I got another job to develop some software for a teacher at my school I was able to run a Z80 emulator to develop for CP/M and get performance several times better than any real Z80!
I loved programming it too, the 286 had some 16-bit data paths that the 8086 didn't have which I took advantage of in assembly and in copy/move/zero routines that I used with Turbo Pascal which I thought was a much nicer language to C but when I got to college I switched to C because it was portable to the Sun 68k and later SPARC machines we had.