Does this watch measure each individual shots? And if so, manually or automatically.

Measure any Shot Distance:
Press on the “Golf Ball” on the HoleVue
screen, then press Mark to record the distance.
Press Mark again to stop measuring.
This is done manually.
This info is on page 30 of the user guide
https://marketing2.skygolf.com/www/INT/sites/default/files/support/products/user_guides/SkyCaddieLX5_UserGuide_062320.pdf