every step in the chain loses power. You lose power just in the power lines. Every trip through a transformer adds some more loss

Reducing the number of transformers, raising the high side of system voltage, and increasing conductor sizes are all ways to reduce the transmission losses. of course each of those requires investments so that's why it can be variable and also something to brag about

Correct. As I recall the did a customer survey and customers didn't like (among other things) the number of power outages. The main goal was fixing that, and several side effects of that resulting in less line loss.