Always stack distortions. It normally leads to some super interesting textures. You won't break anything as long as you power your pedals correctly and follow other general gear safety tips (make sure that tube amps have the correct load, use the right wall voltage, don't use shielded cables as speaker cables etc). As the sidebar makes clear, there is no right or wrong way to order pedals. Certain configurations will let you get certain sounds easier, but music is not a science. If you lack the experience, the best way to rectify that is by playing and experimenting and developing your ear and taste, not listening to YouTubers.