Well, I hadn't invested in any photo gear for years since I was still using film. I knew that one day I had to go digital but that I had to start over from scratch since I was still on the FD system. So I knew it would be a big chunk of cash in the first place just to cover the basics. And while watching the market for the last 10 years or so I knew that I didn't want to compromise too much over what I had before. So any of the cheap Rebel kits from Costco were out of the question.
When I left my last employer last year they still owed me quite a bit of money for vacation days etc. So at that point there I saw 4 options: put the doe away, replace my wife's wedding and engagement rings that she is allergic to, buy a new road bike or buy new camera gear. My wife convinced me that I should go for option 3 or 4 since I had worked hard for it and everything else can happen at a later day (I hope that includes the new bike which is now also kind of overdue given that I've been offered money for my old one recently by a guy who is into "classic" bikes...).
Long story short. I put the money away, lucked out with a few stocks and was able to pull the plug when my local store had its Canon day deals.
Everything I've added since comes out of my little stash that I put aside outside the normal family budget and savings. I wish I was into running marathons, drawing with pencil and paper, but unfortunately, my passions for guitar playing, cycling, photography and so forth are not exactly cheap hobbies. But then again, if you invest in some decent stuff it lasts for decades. And some things can even appreciate in value like I've seen with some of my guitars and amps.