Back when Campagnolo made MTB rims, early 90s, they had angled spoke drillings. I proudly built my first wheel with each spoke coming out of the rim pointing the wrong way then bending. Worked, until I buckled it trying to do 180 degree bunnyhops, then put huge tension in one side to straighten it, then continued my attempts and completely properly tacoed it about 45 degrees.
Re chains – always sized the old chain against the new one, quick job like a pro. Only if you buy a larger cassette, there’s a flaw in the idea. Half way round an epic ride I shifted to big/big and it locked, but backpedalled half a turn and carried on. Some miles later I discovered I’d bent the frame 🙁