"your scenario is making a boat load of assumptions to stand up a theoretical point"
Well, that's the scenario the original post made, not mine. From my experience, this can happen albeit rarely - especially with closed source software.
"specific distro" == The most popular Linux distros don't include old frameworks.
"they then want a specific application and that application has been unmaintained for more than 10 years"
This (for example) eventually describes pretty much 99% of games released natively for Linux, unless one goes with Steam which tries to keep stuff working (I dunno whether GoG or itch also do it).
For really old software, Windows is the best bet. Even if Windows itself doesn't work (it usually does), wine might.
Well, that's the scenario the original post made, not mine. From my experience, this can happen albeit rarely - especially with closed source software.
"specific distro" == The most popular Linux distros don't include old frameworks.
"they then want a specific application and that application has been unmaintained for more than 10 years"
This (for example) eventually describes pretty much 99% of games released natively for Linux, unless one goes with Steam which tries to keep stuff working (I dunno whether GoG or itch also do it).
For really old software, Windows is the best bet. Even if Windows itself doesn't work (it usually does), wine might.