Retrofit windows are tacky and I personally think they lower property value significantly. I would lower a purchase offer on a home with retrofit vinyls by at least $50k just because I would view tearing out and replacing all the windows as a necessity.
Go for a “new construction” window (meaning, you have to tear out the old ones, install, and restucco/etc). On the plus side, it gives you an opportunity to move around windows somewhat with minimal cost. You can easily make windows taller by extending them towards the ground (1940’s homes often had windows that were higher up the wall than current homes).
I did this at my last home, and was able to combine two 40″ windows into a single 96″ wide picture window, because the header running across the windows was contiguous. It was transformational.
