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Shifting procedure/problem

Transmission

Model: 911T, Year:1969, Mileage:237,00, Type of use:Street use only
My 1969 911T has 237,000 miles on the transmission. Unless I'm at a complete stop, shifting into first gear will cause the gears to "grind". Is this normal or an indication that the transmission needs a rebuild? The clutch is properly adjusted and works well when shifting into other gears(except as noted below). Also, when I shift from first to second, it takes what seems to me like an abnormally high amount of force to push the shifter out of first gear and unless I am patient shifting into second gear, again the gears will "grind". Downshifting into second is not a problem nor is shifting into or out of the higher gears. I just got the car and am not experienced in driving Porsche cars. Your thoughts?

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