on some vehicles the extractors can actually get more oil and sludge than the drain plug due to the pan design, someone will have to be the guinea pea and test (i would but i don't have my extractor any more)
Assuming that the dipstick tube location allows you to get the extractor hose to the lowest part of the pan, you should be able to get virtually all of the oil out.
Done this many times on boats (it's pretty much the only way to do an oil change on most inboard engines).
-Spot
This is a good point... Hmnndraining usually doesn't either though
The 1GR-FE has a dry sump oil system. I'm no engineer but I don't think you are gonna get to all the oil out of all those nooks.
Dry sump? I could be wrong, but I don't think that's the case.