This stuff does not matter that much unless you are doing work for print. You still want a decently calibrated monitor though and one that has a good colour range (some laptops and gaming monitors are not really great for artwork at all) If you are doing things for games and work for a target machine, make sure it looks good on that if you can. (Stuff like DS, PSP and so on). If you work for home computers, does not matter what OS really, just make sure you got enough contrast and it looks generally pleasant to you.
I doubt there are many gamers who are not also serious artists calibrates their monitors or has a monitor that is made for doing art on (the highend EIZO monitors are really good btw). So yeah, your stuff will look somewhat different on every monitor anyway, you have to live with that and there is nothing you can do about it.
When it comes to print, yes, you want to have your monitor be calibrated as well as possible, do it every few months, and make sure that whoever you are working with calibrates their shit too, otherwise it is pointless.