I'd feel pretty comfy in the back seat with a 500 foot ceiling, if the guy in the front seat was someone I trusted. No offense to you Jeff, but you won't ever have the time/experience to fall into that category. Guys do this all day, every day, and plenty of them still get into trouble. They are available for hire, at a substantially reduced rate compared to owning/maintaining your own plane, not to mention your skillset. As a bonus, you won't be tied to a plane and wondering if something is going to chew it, flip it over, etc while you are away.
I still get the bug every so often and shop around for planes (I've had the license since 96), but it just doesn't make a whole lot of sense once you start doing the math.
