Ok, since for a virtualization/emulation solution gog either needs to provide a valid win95 (I would suggest win98SE as a better solution, or at least Win95B) license, i doubt releases for windows - But what about Wine and *Nix Systems? AFAIK there are packages available for wine to get Win9x 16bit Apps running even on an 64bit OS... (And installing Ubuntu on an external HD just for gaming purposes ain't that much of a problem)
Or for us, that still have their Win9x CDs/Keys at hand - just the Installer Files/DRM|CP freed CD Isos would be a solution, so that we could install the games within a Win9x VM and just be happy with that.
I'm going to ignore licensing issues here, and assume they're solvable for the sake of discussion, because I Am Not A Lawyer. I Am Not An Accountant, either.
The Wine compatibility layer is an option, but ironies...The effort to port it to Windows has basically been in a move/halt pattern for at least a decade.
Installing some flavour of Linux as an alternate OS is a possibility; but even then, my experience with Wine compatibility has been hit-or-miss.
Installing Win9x in an emulator is a definite possibility, with a few current caveats.
First, GoG is focused on getting games to work on current OS's. DOSBox works well for this as it's basically entirely transparent to the user.
Second, what you'd ideally want for an emulator is software that could boot, run the game, translate calls from low-level DirectX to high-level DirectX, run your old game at 1920x1080p (or whatever), 60+ Hz, and basically be just as transparent as DOSBox.
The second is the much more important problem, because it doesn't exist.
PCem is the only PC emulator for 90s/very early 2000s computers that I know of that's anywhere near completion, and its focus is on 100% accuracy, not speed - Meaning that you can run old games on it exactly as they would run on a computer no faster than about *230MHz, with the equivalent of a *Voodoo 2. Which is amazing...But still has some problems.
Setup - Requires quite a bit, including installing an OS.
Transparency - You have to install an OS. The only upside is that it's not nearly as slow as it would be off of a real CD drive. Enough said.
Overall, licensing aside, there's some issues. Overall, solvable issues, with enough money.
In short, leaving out licensing as stated: Money, money, and time.
* This is being optimized. This is also being optimized.