Is there a way to measure U-values on older windows to determine if replacement makes sense?
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There are already some leaks in the 2x panes (moisture), but they were expensive windows when installed in 1994. They are Marvin wood-clad.
You can get a relatively cheap thermal gun and determine the temperatures the windows are holding. You can also look up the window U-value and give it a rating factor based on age and observed performance. Overall, it is going to be a ballpark educated calculation either based on thermal reading or calculated published values.
Depending on the glass-to-floor-area ratio, cost of utilities in your area, incentives available, and actual ability to improve performance, a window replacement could have anywhere from a 10 to 50-year ROI.