Well, the site and the forum is about; first) whatever Doug wants it to be about. second) whatever Chris allows to be posted without shutting down. So far it seems useful and educational - wouldn't change it for anything but I do participate in many others to fill in what I see as areas not adequately addressed here (though I have recently found I no-longer need to wander around the knife forums;))
Reasonable non-niave individuals all understand that there is risk in everything we do. A cautious individual will attempt to guage the amount of risk. An adventerous individual will accept a higher risk to reward ratio. A prepared individual will spend hours researching, learning, practicing, discussing with others in an attempt to be better at rating the risks that they are taking and preparing to mitigate the possible consequences should the risks be realized. To limit the discussion to gear is probably too narrow for me to feel adequately prepared. To limit the discussion to risk avoidance would result in a less adventurous life than would satisfy me.
Some risks are either extreme or light with little in-between. Light plane travel is one of these areas. Similar to skydiving. In skydiving, if something goes bad - buBye! There is no preparing or mitigating. Unless you pack your own you are really in someone elses hands. There may be some probing questions that I could learn to ask a small plane pilot when he / she offers me a ride but in the end I will either accept "I have looked into the situation and in my educated opinion, we will be fine taking this ride" or not. The result of my being wrong in accepting that statement is a state of un-earned trust. The result of that persons opinion being wrong is near certain fatality. This isn't just fancy liability lawyering. In the final analysis it comes down to how much I trust the individual flying the plane + how badly I need the ride + What alternatives do I have. In the event of a joy ride I may be much more selective and probing in the questions I ask about the safety of the ride since I can forego a lot of joy to reduce the chance of a fatal risk. OTOH, If I am hypothermic and starting into shock from loss of blood lying next to a dieing fire on the banks of a creek barely wide enough for the float plane to land in some remote part of the alaskan interior, I assure you I won't be asking any questions - I will only say thanks to the pilot and my God and add a little prayer for safe passage on the thanks to my God.
In the intermediate cases it is certainly a good idea to have a list of things you might want to know about your prospective flight before you buy the (potentially fatal) ticket. There are preflight checklists that are required of commercial pilots before they are cleared. That checklist itself might give us a good place to start. I am not a pilot and don't have access to these checklists or knowledge of what is on them. I presume that the checklist used by a commercial jet pilot might be a bit more restrictive than that applied to light planes flown privately. Yet a good pilot will do more than the minimum anyway.
things like
When did you get your lisence - how many hours / days / weeks / months / years have you been flying? flying this plane?
What ratings do you have and what do those ratings mean?
How often and when last did you fly this terrain? weather? plane?
What was your experience last time you flew this terrain? weather? plane?
What is the expected weather on the flight path? (if the pilot can't answer this one in great detail then you don't need to know much more)
When was your plane last inspected? overhauled? engine? aeordynamics? controls? instruments?
What types of instruments does your plane have? What does that little meter there tell you? And that one? What will happen if I grab this and twist? How about that?
What sort of survival kit / equipment is on-board? where is it? how does it deploy?
With a private pilot you should be able to ask these sorts of questions with some enthusiasm and curiosity and get them to expand on their ego at length. If they seem confused or hesitant in their answers then they may be poorly trained or unfamiliar with the controls of the specific plane. (that would be bad)
If you have the time over a pre-flight coffee to shoot the sh*t then you might ask them to tell flight stories - What was your worst flight? What did you do to get through safely? Ever had an off-airport landing? What was your first flight like? What was it like in flight school? What goes into a flight plan that will clear the control tower so you can take off? Do different airports have different requirements? Do you have to get certified in each state you fly over?
For me it is about getting to a point where I trust the pilot and his judgement more than it is about trying to second-guess him. I don't have the training or the time and money to get the training to be able to validly second-guess a trained pilot and what is safe for one may not be safe at all for another.
I am sure that there are situations where even the best pilot would be attempting the heroic to fly. Knowing how to spot those situations would make a difference - but only in the extreme cases where it is obvious. It seems likely to me that a larger number of accidents are caused by inexperience and incompetence rather than by extreme circumstances.