I always drain the oil cooler, if you're already making the effort to change the oil why not drain the cooler? I installed my GTM oil cooler with the fitting pointed down so its pretty easy.
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2009 Carbon Fiber/Red 370z aka Trish: Sports Package, Meisterschaft full catback, Fast Intentions Longtube Headers, Injen Long Tube Intakes, UpRev Tune: Sold 
2008 Lotus Exige S Club Racer aka Bella, always leaves me smiling
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