I think you have to be at least a half glass filled sort of person to enjoy this sport/hobby/activity or whatever it was decided it was called. On a rational basis, is there anything crazier to put your money into (within reason)? It's definitely all worth it to me once the sled is fired up, but the costs and fickleness of the machines, the travel, the shortness and unreliability of the season, the constantly changing conditions, the last minute planning...you almost have to be crazy to get into snowmobiling! I think it's just a sickness that can't easily be cured.
My kids are of the age where I'm not going to be able to get out a whole lot for the next couple of years, yet I check the forecasts and this site each and every day, and dream of the next trip....