When I was pure n00b, it was drilled in, don't-fly-with-out-rebuy.
To me this means more than just insurance costs. It means, don't fly anything you care about in a dangerous situation. Most notably in open with a cargo hold of opals when broke, or explo data, or 400 jumps from nearest re-spawn, or super-duper-amped-about-latest-huge-community-event. And it even applies to high G landings in solo with that explo data.
To me it means, if you've put yourself into a situation that would hurt your feelings for more than a few moments to lose, then you've not navigated the waters well. (And most of us, myself including, have to learn this the hard way at least once).
No shame flying in solo. Utmost respect for open only pilots but I fully admit to doing it myself for things that would suck to lose (at this point, almost entirely long research for the details of a particular play/BGS dynamic, or a tedious Engineering grind/gather/build session).
I deliberately exclude PG in this. Unless it's literally 2-6 close friends, they're all still just randos on the internet and I don't care if there's a TOS and some article on kotaku tells me it's safe. Randos on the internet do randos on the internet things.
I've improved a lot in skill since pure n00b, but nothing has increased my fun factor more than not getting emotionally attached to any ship or cargo [I am guilty of being emotionally attached to certainly gameplay ;-) ]. It's a game, and a pretty damn great one, or else we wouldn't be here.
o7. hope my sleep deprived babbling strikes a chord somewhere. And I know not everyone does (or should) play like I do.