My main box has been windows free for 2+ years.
The only thing I thought I'd miss is a linux version of Quicken. I tried many things to compensate for this from win4lin to codeweavers.
Instead of reinventing the wheel, it was easier to site in front of OO spreadsheet and design a budget and financial tracking template. Which has been a lot easier for me to plan and track, and more personalized for me then quicken ever was. Online banking can be done from any browser in my case so that was never a need in Quicken for me, just a convienience.
The updide of that is Quicken has reverted to licensing tacktics and upgrades annually. (my sister still can not let go).
So in addition to being windows free, I've save about 3 upgrades of Quicken and Quicktax.
Once you make up your mind to see the computing world without windows, you will find a way to accomplish the same tasks.
Gaming may be a whole new ball game. (or obsession)
I think if you are 'thinking' about going windowless, you are ready, JUST DO IT and learn to have fun.
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