This.

You get some gear. It's nice, but heavy...then you realize there's so much lighter stuff out there.

$100/lbs later your congratulating yourself that your base weight is 15lbs until you add food and water, and you realize that your pack still is too heavy. You finally shave off another 2 lbs by buying all new luxury items at $30-$50 a pop, and getting a lighter stove.

Then winter comes, and that 4 season, dyneema tent looks mighty appealing. Not to mention you need a better rated sleeping bag (cause that hammock ain't gonna cut it) and a pad, a better puffy and fleece, crampons, maybe an ice pick, and another stove that works in the cold...

Edit. Damn it, I forgot I need new shoes...even if I wanted to brave it using my summer pair, those trail running shoes are destroyed over the course of 1 season.