Think about this: as a civilian, your second line gear is probably for supporting a rifle and other fighting activities. In the guerrilla example that you gave, by dropping or caching your overt fighting gear, you still can have your short-term survival, navigation, gear on your person. This allows you to escape and evade, and to disappear back into a civilian population: e.g., the gray man concept.
The point, both tactically and organizationally, is to be able to scale your gear as necessary. Mission drives the gear train. Less gear means lighter, faster, and stronger, so long as you haven't compromised any mission-essential equipment.
First, what are your essential tasks? Second, what additional capabilities can you afford (money, time, weight, size, visibility)? Finally, how can your gear be configured to meet those needs as efficiently as possible? Many of us need to spend more time on the first two questions before dwelling on the third, but as gear guys, that's not as much fun.