Honestly, I think a lot of people get their pilot license only because they are really rich and can and have the want and means to do it, and they are motivated by how it makes them seem more worldly and sophisticated. But there are people who genuinely love aviation, and are motivated by the love of it to maintain a plane and use it.
I have two friends who have their own planes and both are small planes. I think both are five seaters. One of them is snootier about it than the other, but both are really great guys and while I haven't gone up with either of them, I would trust either of them completely. In fact, my son is staying with one of them this week and is flying with him in the morning. My son has flown with him before, and yes, it makes me nervous as hell, but it went fine all the other times, and I know it will again. If I didn't trust the friend completely, I would be nuts about it. I really don't look at it much differently than when I fly with my son on an Embraer to Chicago.