> The reason you need to run a 16 bit installer is the software isn't free or open source therefore a simple recompile with a newer version of debhelper or whatever isn't going to bring it up to modern packaging standards.
On the other hand, the old windows software in question will most likely actually run. Debhelper is irrelevant: confronted with a package of comparable age on Linux, you'll be digging up the source code and trying to make it build, not merely tweaking the package, with all its ancient dependencies.