1). I don't think I've gotten to that point yet. I've always led a relatively austere life, by choice, so I don't have a heck of a lot to divest myself of. Most of it I'd give up without a fight as it doesn't have much monetary or sentimental value. As for my cars, I could probably downsize from a 1yr old Cobalt to something older to free up some capital. I'd like to say that "You'd have to pry my cold dead hands off the steering wheel before I sell this Corvette", but the wheel is in a box with some other interior parts. In all likelihood I'd end up taking a loss on the car given the condition that it's in now. Nonetheless, if it has to go, it has to go.
2) I think about this all the time, and in one aspect I've begun doing just what you say. When I got the Vette I basically postponed the idea of, if not gave up completely, the concept of finding the right girl, getting married, starting a family, etc. etc. I want a mate like there's no tomorrow, but I'm 28 years old and it's apparent that it ain't happening anytime soon, so there's no point in waiting for it when I can a) enjoy the things that God put on this earth for me to enjoy and b) do what I can to make others around me better. This wasn't really a random change-for-the-sake-of-change, it took a couple of years of deep thought and prayer to realize that this course of action is the way to go.
As for my job....well, it sucks to varying degrees each day, and at times I wonder whether or not this field is really for me, but the fact is that it's just a job. It pays for the life I really want to lead, and gives me ample vacation time to boot. I'm at the point where if they want me to run on a giant hamster wheel all day, I'll do it with a big smile, then go home and do something more enjoyable. So I'm not exactly jumping at the chance to leave right now.
I don't know if my story helps any, but if I can offer some advice, I'd say to take some time for yourself..remove yourself from the "status quo" for a short time (5 days to a week or so) and retreat to a place where you're free of distractions to get in some deep thought. I know you've said you're not a religious man, but don't be afraid to ask God for guidance if you seek it.