I like to change the transmission oil every 30-40000 miles and always put one in so I don't have to change the filter and oil pan gasket every time. The manufacturer's change interval on my car is 100,000 and I can't wait that long to change this fluid. The only problem I see is that the plug is about 3/8" in the sump so the 3/8" fluid doesn't drain. I think the only way to avoid this is to weld the cork. In any case, changing some fluid every 30,000 is better than nothing every 100,000 in my opinion. Make sure the drain plug isn't blocking anything in the sump (with the filter installed) before drilling, set it to the bottom of the sump, put teflon tape or fluid stick on the pipe plug and deburr the drilled hole otherwise the gasket may close not (common practice).
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