another reason why i don't want to use modern tools is that, say, the easy path of using DJGPP with GDB et al which you can already get an extension for is that DJGPP requires 386SX minimum because it doesn't make true DOS executables, but rather 32-bit protected mode binaries and i want to support XT-class machines
ohhhh there's a GCC fork that can produce IA-16 binaries.... 👀 👀 👀 https://github.com/tkchia/build-ia16/releases