Honestly, I think you should have good reasons for switching to GNU/Linux. Freedom to change the software, freedom from proprietary headaches, and to a lesser extent, low to no cost are good reasons. A quibble with Windows interface isn't good enough imo.
It sounds like you aren't really /into/ computing, and haven't developed the skills to quickly work through problems. What I'm getting at, is when you need something for work 10 minutes ago, having your unorthodox system go down will be a real problem. Panic will set in, followed by frustration, and people getting pissed at you for not producing.
Modern distros are pretty easy to deal with, and don't take special knowledge, but they aren't meant to run Windows software. In many cases that can be worked around, but it takes special effort, and someone who isn't into computers, or has no real good reason for switching won't be inclined to put in that effort.
All of this is my opinion, and I may be misjudging your posts, but it's to save you grief, and to save the image of GNU/Linux. If you install something unsuitable for your uses, you may assume GNU/Linux is a junk O/S, and a cheap knockoff of Windows, when it was really the wrong tool for the job.
If you really think you're interested, my suggestion would be running it in a low impact machine. Something you don't need for work, or that doesn't have software you REQUIRE. Play around, and get used to the differences, and see what it's about. If it's something you think you want to explore more, you can think of trying to get Windows programs running, dual booting, or using VMs. It'll be your schedule then, and your livelihood won't be dependent on getting things going.
