On my machine I run a dual boot with Win 7 and a Linux distribution called Zorin. Zorin is designed to look a lot like Windows, so it makes it a little easier to feel your way into Linux. IIRC the dual boot feature is part of the Zorin download.
Linux is useful in resurrecting old Windows programs that will not run under contemporary Windows OS's. I like Office 97 for example, pure nostalgia, and I was able to bring it back alive under Linux. Windows 7, including its virtual XP operating system, cannot or will not run Office 97.
The parallel to your v.14 problem is the date, 1997. I think 1997 was also the date of issue for Autocad v 14. So it might be worth a try. The Windows OS in 1997 was Win95.
The windows emulator I use under Linux is Wine. Here is a report on how it fared on a trial with Autocad v14.
https://appdb.winehq.org/objectManager. ... on&iId=103In my experience emulation can be made to work, sometimes, but it is not quick and easy. On the other hand, because it is a big project, it is one way to learn how to navigate and use Linux.
Another way to recover legacy files and/or run legacy software is to find a Win95 laptop on Craigs or ebay. I bought a refurbished Win95 machine here:
http://www.laptopoutlet.com/delad8uslap4.htmlI used it to recover some legacy database files. This one shows Win XP but a Win95 machine is probably available.
All that said, it might be time better spent learning one of the free modern CAD programs, e.g. Draftsight or Sketchup. I notice Autodesk's Fusion 360 program often has substantial discounts for students and hobbiests.
Michael