Cripes, Matt! Your post would make an excellent LSAT or MCAT question.
On a more serious note... Cebreez'z links are excellent. The Which Chain Of Effect Pedals Makes Life Easy? one-pager by Keeley is awesome and aligns with most of what I've read over the past 5 years. I think it's conventional wisdom now.
That said, don't be afraid to experiment, especially if you're curious or inspired. You should learn rules and master conventions so you can break them.
Nothing is anything until it is written. After that, it's everything.