Never have I regretted spending money on airplanes. The costs for upgrades and maintenance may have been prodigious, but they always felt good. The airplane was either improved or restored. I never questioned these investments. Same for hangar, insurance and fuel. I wanted the airplane protected indoors, I wanted to protect the people flying in it and I wanted to use it. Even in the days when I had bought a new house and neglected to sell the old one and had a note on a Cessna P210, I wasn't scared and I wasn't desperate. The old house sold after a year, the note got paid off eventually and all during that time I was high and pressurized. I've liked looking at the logo of the Jeppesen bill or the invoice from Aircraft Engineering. Rather than a depressing recurrent expense of little recognizable worth like health insurance, say, I always felt good, solid, right about airplane costs. No doubt this kind of thinking could have been easily criticized from a financial point of view, but it was unassailable emotionally.