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Hi Lordblood, long time no see.
Grinding when going into second sounds like worn synchros.
I would:
Drain the gear oil through a screen and have a look with a bright light. If it is reasonably clean, replace the fluid with OEM and also replace the clutch hydraulic fluid. Maybe you got lucky.
If the screen looks like shiny grenade fragments and lots of metal, fluids alone won't work. At this point you can get a quality rebuild done for about $4K, or find a clean used trans at a dismantler for about $1400.
Good luck!
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2009 Cayman 2.9L PDK (with a few tweaks)
PCA-GPX Chief Driving Instructor-Ret.
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