I only have 15 machines so far, so obviously I'm just getting warmed up!
I got into old machines from being a quilter. I wanted a Rocketeer even before that, though, I saw one at a friend's house but didn't know really what it was called or anything about it other than it looked awesome and I wanted one. But I wasn't really sewing much at the time and didn't search one out and sort of forgot about it. Then once I got into quilting and started getting exposed to vintage machines at classes and such, it got me interested again. It started with finding an old Pfaff like my Grandma's - the machine I learned to sew on. Then I found a rusty, beat up singer 15 for $20 and decided I wanted to try to restore it (still haven't done that). Then...well. It just went on from there!
The more I learn, the more machines I want! But for me, the hunt is at least 50% of the fun. I wouldn't want someone to just go down my wishlist and hand all of those machines to me, that would be disappointing and no fun at all.
It's gotten to the point where my sewing room can't serve as my sewing room anymore because it's too cluttered with machines and spare parts! SO, we're in the process of cleaning out another bedroom upstairs that was just being used to store extra furniture and suitcases, and that's going to become the "indoor shop" where I can twiddle on sewing machines and DH can twiddle on his old radios.