I didn't think the 8086 programming model was that bad. There were several different memory models for compiled languages and I think it was outright fun to work with the segment registers in assembly language.

It was tragic though that no "Multitasking DOS" emerged in the 1980s. My 1987 AT clone was more powerful than the largest PDP-11 but the big PDP-11 could support 32+ terminals. It was annoying as hell that I couldn't download files from a BBS while doing something else -- I tried to make a TSR that did that but couldn't make it work.