I really do not wish to curse myself (so any gods, Murphy, any master of fate listening, please don't curse me, it's not my fault there are no finger crossed or knocking on wood icons!), but there has been some progress here. I have been taking things VERY slowly, and I am at a point that feels momentous. THE TIME-SERT IS IN!!!!
All the worry about lining up the drill bit turned out to be unnecessary. After about the first two mm, it couldn't be wiggled if one tried. It just cut in and carved a clean straight path the whole way. The point near the back where it started turning the engine wasn't as big of an issue as I feared either. Yes, I took off the fly wheel inspection hatch and blocked the teeth there AND took out the spark plugs and blocked them too for safety (hey, I wanted to change plugs anyway). After the drill, I cleaned the hole, ran my magnet through and waited for the brake cleaner to dry while I inspected the rest of the car. Then more cutting oil and the counter sink tool. More cleaning, then the tap. I stressed and stressed about getting it lined up just so, making sure I could put some leverage on it (but not too much!), and more cutting oil. Well it turns out it will bight in straight and not budge either after the first turn.
But it cut just like butter. I mean very smooth, all the way to the back of the hole. Then I cleaned some more, and extra good this time. Several blasts with brake cleaner to get all the oil out, as well as several swabs with lint free bits and several passes with the little magnet. Test fitting the insert, it went in just as clean as you can hope. Double checking that the hole was clean and oil free, I put the high temp, most permanent thread locker on the insert and ran her on home by hand and it went in all but the tiniest of a fraction. Oiled the insert tool like the directions say, and with a slight hesitation, it sat in completely flush and VERY tight. I immediately swabbed the oil back out to make sure it does not seep around and interfere with the thread locker, and now I am waiting for it to set up before I start putting the car back together. I sure hope I am done for an awful long time!