It really was the wild west back when 9x was popular. I'm genuinely surprised they ran as well as they did. NT was a vast improvement.
In my opinion the lacking memory protection was not about the architecture itself but about the fact that it was meant to be single-user and thus there were no permissions. IIRC from Win32 code you had to jump though some hoops to be able to access whatever memory/hardware you wanted (ie. you could not overwrite random non-owned memory by mistake), the fact that you could do almost whatever you wanted in vm86 code was essentially an feature and that Win16 code could access any other Win16 process data was weird design decision that is also shared by all NT versions up to 2000 (where it is configurable).
Hey, I actually liked that! Back when Internet was young and the OS was single-user, I felt like I had more control over my own machine than I do now. Being able to mess with other processes' memory was a feature for me :).