Winter 2009-2010In the past, I've had moderate success extracting the oil via the dipstick.  I've never been able to extract it via the extraction tube.  While winterizing this year, I had no success, period.  I tried my electric oil change pump, a Jabsco hand pump, and a vacuum pump -- no luck.  I started inquiring of other Cape Dory 28 owners, and learned that it should be much easier.  In particular, I watched Mark extract the oil from Brandywine's Volvo engine (via the extraction tube), and I was astonished at how quickly and easily it was done!  Clearly, there was something wrong with the extraction tube on ours.  I soon concluded that it was clogged, but was not able to unclog it using a wire.  
My next strategy was to worm my way underneath the engine and remove the drain plug, planning to replace it with a drain kit to make future oil changes easier.  No go:  I could get a large wrench on it, but the plug wouldn't move, at least not with the limited leverage I could get in the tight space.  (And, sadly, I think I injured my back trying.)
We were planning some professional maintenance anyway, so I added the extraction tube to the list.  During the winter, we had Dick Vosbury come down to do a few things:
- Removed and clean the heat exchanger.
 - Remove and clean and oil cooler.
 - Replace the alarm unit on the bridge.
 - Clear the oil extraction tube.
 
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