Homemade Olive Oil?

Has anyone ever made olive oil on a homestead scale? There is a lot of info out there about pickling/marinating olives for eating, and I'm doing that with some gleaned olives, but nothing at all about pressing oil on a small scale. I will have 4 or 5 trees in my system and it would be great to have both eating olives AND oil. My current thinking goes in two directions....mash them up and boil the mash, hoping that the oil will rise to the top, or, rigging something like a cheese press, perhaps using a car jack somehow.....

You want to press them. Boiling will degrade the nutritional value.
I haven't personally pressed, but I have brought olives to be pressed. The way it worked there, if I recall correctly, was that the mash was laid on burlap that was laid inside/across a wood frame till the frame -- I can't remember if they were 1x something or 2 x something -- was full. Then the burlap was folded over, and the next frame was set on top of that and filled, till the stack was the maximum height (or less) for the press. Some large sturdy lid that fit inside the frames was pressed down on all -- remember the burlap was not attached to the wood, so it would just flatten inside the stack of frames. Does that make sense?
I can't tell you what psi the press used. The liquid coming from the olives was collected in tanks. The oil rose to the top. Sorry, don't remember details of separating -- this was in the seventies.
Might be able to scale down for homestead use.

seed oil press plans: http://journeytoforever.org/biofuel_library/oilpress.html

Same as many briquet presses for turning sawdust into duraflame-style logs. That means the compound lever press should work, too. http://home.fuse.net/engineering/ewb_project.htm

Olives do not need that much pressure, so a cheese or wine or cider press should work.

I wish I had a good source of home-grown oil.

I have a piteba pressa and have used it on nuts and seeds. would like to try olives but they aren't a local crop so I guess I'll never get the chance to try it.

I've been thinking about this too, and after talking with a farmers market olive oil vender who takes his olives to another site for processing, I too am interested in finding someone with a good press who would do this for a fee. I may actually plant some olive trees if this were a cost effective venture.

There is a farm out of McMinnville Oregon, north of Salem about 25 miles, that is now raising olives. I understand they're growing well, but the trees are only about 3-5 years old so far.
My son set up a 12-ton hydraulic press for me to make apple juice. It works like a charm, and is so much more efficient than the pretty round oak apple juice presses. I get 5 gallons of juice from 15 gallons of whole apples. If I could get enough olives, I'd definitely try pressing them with this contraption. I explained our process with pictures here: http://www.homesteadingtoday.com/country-homemaking/preserving-harvest/419804-pressing-apple-juice-hf-12-ton-hydraulic-press.html
I watched a TV program about pressing olives with a small-farm press, and thought my Harbor Freight press should work, although it may have some waste.
Kit

That's an amazing machine. I'd like to know if it can process olives when you find out.

We're planting olive trees right now (Koroneki and Coratina) and plan to use my 20T shop press with my large cheese mold. That way I don't have to buy anything new.

http://www.harborfreight.com/20-ton-shop-press-32879.html

2 answers to your question regarding home made oil. Its possible to buy and amazing oil expeller from www.piteba.com it is designed fro pressing ol from seeds, such as sunflower seeds, and has a fairly high yield. It is designed for 3rd world micro business, so people can make and sell oil and oil seed cake for feeding livestock from their own grain. It will make great oil from sunflowers (the black seeded ones).
The other answer is for the olive oil.. Lay your fresh olives on a tray in the sun for 10 days to dry, turn them twice a day.
Use a cider press to press the oil out.
Line the cage of the press with a nylon mesh bag. Fill to within 3 cm of the top. place a bucket under the spout. Ratchet down the press. bright green oil will start flowing out. Keep the pressure on until there is no more oil coming out or you hear the pits start to crack... they make it taste bitter, so stop then. Let the oil settle. Any water present will be at the bottom. The drying process you started with should have eliminated most of the water though. You can use your oil immediately.