Biased opinion only!
Once tried Linux Mandrake with Win 98: eventually had some success in dual booting, but as it's a totally different OS, and the look and feel is different, it became an interesting exercise.
If you drop a b0llock, it's difficult to get back to Win 98 because Linux writes to the boot sector.
Also had difficulty getting a number of drivers for scanners/modems etc. (non written for Linux!)
If I had the time, I'd acquire an old machine - even an old 486 will do - and set up Linux as the sole OS, and have a play. Then take it from there. Might save a bit of angst!
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Me, sweat? I'm that cool, it's condensation.