12 hours ago, Chris Hennes said:The trick is that olives inhibit the formation of gluten (presumably due to their salt content)
Salt is a gluten enhancer, not an inhibitor. Fat is an inhibitor. To a lesser extent, particulate matter (small pieces of olive) will inhibit gluten as well, although it won't inhibit it as much as bran, which, because of it's sharp edges, bran cuts holes through the gluten. When it comes to inhibition, bran and fat are the big players.
Did you puree dry or wet cured olives? Both will require very different approaches because of the varying composition- dry will have less water and more fat. If the recipe is tailored to one, using the other will effectively break it. Dry cured olives in a wet cured tailored recipe will produce a dough that's too dry, wet cured olives in dry cured tailored recipe will produce a dough that's too wet. In a previous post, you talked about building an 'experience base.' This is one of those areas where experience goes a long way in resolving issues. A precise recipe helps, but, if you know you're adding water (wet cured) or fat (dry cured), and you've added water or fat to doughs before, you're in a better position to course correct.
12 hours ago, Chris Hennes said:So my question to you all (and one I could not find the answer to in the book) -- how should I have mixed the puree into the dough?
The simple answer is 'earlier.' 
Assuming you've adjusted the formula properly for either wet or dry cured olives, then, you'll want to add a wet cured olive puree pretty early- possibly even close to the start. For a dry cured olive puree, with the inhibition the extra fat brings to the table, then you might want to go a little later, such as when the dough starts coming together. In some high oil pizza doughs, they incorporate the oil about 1/3 to 1/2 into the total mixing time. If, say, you're mixing a total of 10 minutes, then 4 minutes might be the happy place. If you're up for the math, you might want to calculate how much fat you're adding with the puree, and how much total fat the dough will have. In my experience, anything below 6% fat, with a strong enough bread flour (see below), requires no late addition.
One other thing you might look at, both from a perspective of potential overmixing and elevated fat content, is a higher protein flour. You don't need to necessarily go crazy high with something like Sir Lancelot (14% protein), but, if, say, you're using Gold Medal better for bread flour, which clocks in around 12%, that's going to break down more quickly than KABF (12.7%). Even 12.7% might not be ideal for a higher fat loaf like this, and a slight bump to, say, 13.2% might perform better. You can't knead any dough forever, but, it sounds like if you had the right protein flour, you could have worked your dough quite a bit longer without having it give up the ghost like it did.
Edit: My strong flour advice is only applicable to commercial yeast leavened formulas. As you move into the gluten enhancing effect of natural leavening, you won't need quite as much protein in the flour. Natural leavening doesn't give you unlimited strength, though, especially with less detectable acidity, so, for an especially high fat naturally leavened dough, a stronger flour might be beneficial there as well.
Edit2: I remembered something else. Water + flour + time = gluten development = more difficult addtional ingredient incorporation. Since the recipe you use states 'direct,' I'm assuming there are no rests involved prior to adding the puree. For any late addition, you want to stop the mixer, immediately incorporate the ingredient, and then return to mixing.
