How do you know when its time to replace windows?

Updated: July 29, 2020

I had a contractor give a quote for some minor renovation work, while he was here he said my upstairs windows were very old and should be replaced. They have wood frames and they are for sure old, but they at least have two panes of glass. Should I follow his advice and replace them? I can do it if I have to but its going to be at least 15k that I’d rather not spend if I don't have to. Thanks in advance.

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