For the right-clicking the Stop button on Mac did you try all the qualifier keys - Ctrl , Opt, Command ? It should be one of those. The option ‘should’ stay checked once you check it, so you shouldn’t have to select it every time. The option is called “move cursor back to start - after standard playback”.
For looping, I’m not the best to talk about it because I never use looping, but there’s probably a more permanent standard way of having it enabled to play only the selection when you have a time selection. Maybe check the manual.
Also the manual says on page 112 that there should be Montages in LE. I doubt you can add effects to montage clips in LE, but you should be able to at least create a Montage.