I don't fully understand how upscaling low resolution would give better readability for many small windows on the same screen? I know Nvidia's DLSS but isn't that made for running games at a small resolution and stretching/upscaling that to fit a far bigger monitor?
Gotcha, DLSS/Super Resolution just don't seem to fit the OP's question at all though. The monitor scaling I replied with would allow to fit more windows on the monitor (though they will appear smaller as they'll have less real screen space while having their old virtual screen space). I don't understand at all how DLSS/Super Resolution would be related to that.