I've never been to Oskosh, so I can't speak to it - for me the EAA is the local chapter and other members from different chapters, and I'll bear witness that safety is the thing that gets asked and talked about first and most about builds and flying.
Pitfalls and hazards are grist for the conversation mill, and not in a bragging sort of way. We tend to talk about when things could have gone badly and how we got out of them.
My personal limits are simple - if I wouldn't play on the golf course pulling a cart for 18 in the weather I won't fly over it in an airplane. Not to say that I haven't had weather turn to the yuck and put my chicken butt on the ground with all haste, mind you.