Changed gear oil in my 2000 S about four months ago.
Three challenges I found were: 1) Removing the braces and pans that stabilize suspension and protect trans-axle. I had not carefully read the article in 101 Projects before I got under the car describing their removal. So that surprised me a bit. 2) Getting the drain plug and filler plug loosened. I had use a ratcheting tie down strap attached to my truck at one end and the socket ratchet at the other to produce enough force to loosen the drain plug. Would suggest a breaker bar as best tool to use but mine was too short to assist me and my efforts. 3) The viscosity of gear oil and a hand pump while laying on one's back under a car on jack stands will work muscles one normally does not work. ;-)
Also, 2000 S only requires one size hex for both plugs. Other models and I think years require two different sizes and/or styles. Be certain you have correct tools before you begin.
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2000 S
Metallic Black over Boxster Red
6-speed
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