We're replacing a few windows in our old 1920s house. The windows are original and the wood frame on one of them has had water intrusion through the frame. We even had a water bubble last year that we're pretty sure came from water through the rotten frame.
We had someone come out who specialized in restoring these old wooden windows (was too expensive), and he said if we ever did replace them to make sure we did a full-frame installation because the originals had no flashing and he saw the water damage.
We've had about 5 companies look at these so far and more than half of them have said we don't need a full-frame replacement and just want to do a retrofit. It's obviously cheaper to retrofit but we're wary of doing that to only continue having water intrusion issues afterwards. Are we overly concerned about this?

