Start with safety (steps, paths, entrance), then accents (trees, walls, facade). Avoid glare for passers-by and neighbours: aim down or at the object you light.
The low-voltage transformer steps the outlet's 120 V down to about 12 V. Add up the apparent power (in VA) on each fixture's spec sheet; for LEDs it is often higher than their wattage. Then choose a transformer well above the load: common practice is to stay under about 80% of its capacity, and some makers ask for less. The transformer's manual has the final word.
Cable loses voltage along its length: that is voltage drop. For a two-conductor cable it is about 2 times the length, times the current, times the gauge's resistance per metre. LED fixtures work within about 8 to 15 V, halogen within a narrower 10 to 12 V. Heavier cable, shorter runs or hubs keep the last fixture inside its window.