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1 High end card is the way to go.
1) Two medium cards need SLI/xfire mobos, so some added expense there.
2) Two cards always have some performance loss... its never x2 performance.
3) If you do already have a mobo that will handle two cards, buying one faster card will give you the ability to upgrade in the future more easily by just dropping in another high-end card.
Which option would give better performance for someone that does 3D modeling / video editing?
Reread the OP. His budget is $300.
neither will give you better CAD/3D Modeling / Video editing performance as the programs take advantage of quadro/fireGL cards and not standard GFX cards
seeing as you have a 20" monitor with a max res of 16xx by 1200 or 1050 then 2 cards are a bloody waste at the moment
a single 280/285 would do you more good now, and if you upgrade your monitor later grab another 280/285 then if you feel like you need to.
even a 260 216 would be enough for you now
Thanks for the informative responses. I have settled with the Quadro FX1700