> leads me to think philosophers lead blessed, problem-free lives.

I agree, perhaps with the qualification of 'eventually', having been both of these people:

    1) someone born dirt poor who had to spend every waking moment to feed myself
    2) someone who can pontificate in comment sections 

As my life became more blessed I could afford more philosophy.

Those who can't do, teach. Those who can't teach wander philosophically.

Playing with ourselves. Man plans, god laughs. Everyone has a plan until they get hit in the mouth. I could go on.