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No one can realistically help you make this decision.
The 244 is worth more than the 9-series because of it cult car status.
Most 244's are more fun to drive.
A wagon is more "valuable" to the owner as an only car.
The 940 is marginally easier to work on.
The 1985 244 has some parts that are getting near impossible to find.
"Since it is so straight and pretty, I worry about door dings and rock chips." Will your life be happier (mine would) without this concern. Owning a "beater" is very liberating in this way.
I have said it before in other posts similar to this but you need to make a list if why you want to keep each...on paper. Then figure out what is more important in your life from that list.
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