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There's no point checking the same thing 3 times, check it once, and do what you need to do there, once.
while true
do
echo "Would you like to quit? [Y/N] "

read ANSWER

...

This is not Unix/Linux. cygwin is a Linux like environment for Windows. Windows is in this case managing your windows. Cygwin is just being started in a cmd box of Windows so Windows applies^^. So...

That window looks like a Windows command window. You should be able to right click on the title bar and select setting for editing etc. (only got the German version here sorry). Hopefully you should...