So I think I've been going at this for 2 and a half years now. I recall having a load of extra cash 3 Christmas' ago, an empty bookcase with maybe 6 books on it and my old DvD collection. I was addicted to WoW, DvD's were being replaced with this newfangled Blu-Ray or them HD-DvD's(who could win?!), so I really had nothing to spend my hard-earned cash on. A trip to the comic store across the street with my roommate one day yielded my first toy(since I was a kid, though I also did Warhammer through my teen years, so did I ever really stop?), DC Direct's Red Son Batman.
I don't know how much time passed between the first and the second, but at some point I picked up one of the 25th Anniversary GiJoes, my old favourite toys, and fell in love again. One Joe turned into an Army, and soon my books and DvD's went into the closet to make more room on the bookcase for figures. I started visiting toy forums, and the internet showed just how much toys had changed. Six months later I had ordered my 1st Revoltech and Figma from Japan, then my 1st Shinki, my 1st Marvel Legends, my 1st MotUC, etc. Then one year later I got my 1st 1/6th figure as a present for myself, Sideshow's Clone General Obi-wan Kenobi, 2 weeks later he tumbled off a coffee table and broke his ankle joint, and a month and a half of no luck finding a replacement myself I came here to ask for help. Someone here sent me a spare joint free of charge, even refusing payment for shipping, been coming here since.
Then to now I've tried a lot of different toy lines, I try to dip my figure in everything. I haven't bought a 1/18th figure in a loong time, I still buy Japanese figures as I'm a pretty big anime fan, and I'm still refining the 1/6th collection(limited to only 2 detolfs of course, always just 2 detolfs..) I love this hobby.
tl;dr: I started with the small toys and then sold the small toys and bought the big expensive toys, expensive toys are better!