Yeah on my SF86 I listed all the dumb shit I did and the investigator called obviously kind of concerned but receptive. We went through each one and his key point was "do you understand you can't do that" and as long as you answered yes, documented it on the form ahead of time, and it was obvious you weren't lying through your teeth then pretty much anything you did that wasn't in the last 3-5 years was pretty much immediately forgiven.

Some security officers are really touchy on these kinds of things and will tell you to exclude or lie but investigators pretty much never care what you did as long as it is obvious you don't plan on doing those types of things again or being an active problem.

They just want it for their records and they want you to be an open book such that they don't feel you are concealing anything problematic.