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Default Window replacement dilemma -- please help

Hi,

I live in a 100+ year old house that has the original windows. They're
drafty and inefficient, so it would be nice to replace them all (23),
but there are a handful that are more urgent due to failing mechanics
or rotting. The thing is, we'll probably be selling the house within
the next five or so years, so am not sure what is the best approach to
take. One plan would be to spot replace the worst ones first, then do
the others when convenient, which may or may not result in the whole
house getting done by the time we sell. Another plan would be to just
buck up and get them all done at once, however, if we sell sooner than
later, likely won't recoup much of what we spend. There's also the
issue of quality. If I just patch up the problem ones with a few lower
end vinyl replacements (which would still be much better than what's
in there now) would that reflect poorly on the house when it comes
time to sell?

Thanks!

 
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