First of all: if you are going to buy a set of extractors, buy the best ones you can afford. I tried to remove a broken exhaust stud in my Sanglas 400Y and the extractor broke! so I had to remove a broken stud with a piece of hard extractor inside!!!
That same bike had the same trouble with the oil plug, but the engine was in the bike. Believe it or not, I used a breaker bar trying to loosen it and the bike would rotate around the centerstand!!!! I needed a friend to hold the bike tight to keep it from rotating until I could loose the bolt that cracked way loose, but fortunately, the threads were perfect, so I just bought a new one and this time I didn't overtightened.
In my CB350 resto, during the engine rebuild, I just noticed the oil plug threads were a little worn, indicating somebody had stripped them. As there was no better time than then, I just bought a lower crankcase out of eBay with better threads and saved me some future hassle.