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Window replacement help - where to start?

We live in a 1930's bungalow with the original windows.  Much as I don't want replacement windows it's time for them.  I'm tired of windows that need to be propped open with blocks of wood, with storm windows that don't work, with windows that can't be open at all, with broken locks, with dirty windows we can't clean, with wind whipping through in the winter, with peeling paint inside the windows, with repairs/upkeep that can't be done without removing everything.

First question - is it worth saving the old windows after they are removed in case the future new owners want "original windows?"

Second question - approx how much do new windows cost including installation (we are not diy's)?  We have 7 windows to start and possibly an additional 4.  I've seen prices range from $200-$6000 per window.  We certainly don't need anything fancy but we do want them to  look nice without looking modern.  

Third question - where do we start? Home Depot did our basement windows and that is out for this project, they did a decent job but what is fine for a final look in the basement won't do for the living area.  Should we go by one of the big names, like Anderson?  I don't even know where to start with this project. Do we go to the window store, do we let them come to us?  What do we look out for?  When replacing windows does this affect anything inside, such as sills, woodwork. Does it affect the woodwork outside the window?  How long does it take to install 7 windows - one day? one month?

We want good, decent windows without  losing the bungalow charm.

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