I change my own oil most of the time now. Very little is required in the way of tools- a wrench or socket set, possibly an oil filter wrench, and an oil drain pan. Good oil drain pans can be found at Princess Auto. I guess the other thing is ramps, and buy yourself some coveralls that you can leave in the garage.
I usually look for oil on sale and get a jug for $10, or $20 for synthetic. Filter is around $5.
For me the over/under for the "pain in the butt" factor is getting an oil change for $30. However most places that will do it for $30 are also places that I have had screw up the change.
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