@Ubiq, I have a similar problem, but with my business partner. I'm thinking of just making a customized Linux stick and sending it to him, telling him to plug it in. He has trouble remembering what a mouse is. So it needs to be 1-2-3: plug in stick, turn on machine, click on lower left corner for menu, with icons on the desktop (horrors for many) that are like he'd see in Windows 7 or XP. Mint lets me wholly customize the menu, so I might do that, too. Set up channels in the browser, have my admin account plus one in his name, so he can't wreck anything, basic functions like copy and move and make DVDs (which Windows still doesn't get right), pre-configured with MS Office 2003 and Plus! to make the Windows colors and fonts attractive (wine makes them default gray). So that he weans off Windows usage directly, but slowly, at his own pace.
Problem is, that's a lot of work for me. I just lost a month due to Win10's rollout: had to test, would it be faster and safer for filing tax returns online or not, only to find out there are a lot of EULA gotchas. For the US Government, much still has to operate on Windows, esp. XP.
So for you, the hassle of what you must do, versus what benefits? Seems like that should be THE criterion, before you ask how do you convince. For how, is by demo. But crafting that demo, takes time.
Then there are the typical turnoffs and questions. BIG turnoffs are the jargon, the holier-than-thou, the constant battle of permissions. These three things are Linux of the past (three+ years prior), and we think that's how it is, still. That Linux is all geeky language and oh how proud the geeks are of Linux and how they look down at Windows users and once you're in it, you're guilty until presumed innocent, having to give your permission all the time, even after being signed in as admin. It's not easy going from a drive letter and name, to 'sda1' and 'media' as a folder where the drive names are stored, to know stuff like 'mount' and 'home' and etc fstab bash and all those words which frankly look like gibberish to the uninitiated. We left DOS, and don't want to go back to terminals.
Parallel to how when someone enters a new faith, or is considering changing faith, he's hit with all the arguments, vocabulary, everyone trying to be helpful but appearing to proselytize, etc.
So a demo 'hi here's what Linux does' live onscreen, is my option. If I can get my business partner to know how to click on the play button.
Edited by brainout, 05 August 2015 - 06:41 AM.