*I started out getting some games as birthday and Christmas presents (Black Box D&D, HeroQuest, and The Lord of the Rings Adventure Game).
*Then I started buying games from the catalogues or pamphlets that were included in those games via mail order. I needed a check from my mother to do that.
*Then there was a buying freeze for many years as we just played what we had (mostly Rolemaster Standard System RMSS) for about 8-10 years.
*Our local mall got a new gaming store called Bill & Walts Hobby Shop and I started buying AD&D / Ral Partha metal miniatures, and eventually got a few other games.
*Waldenbooks and Kaybee Toys also became spots in the mall that I hungout in a good bit, and I bought a few items that I could afford. I wish I owned a lot of those books and games today... Sigh.
*I paused on RPGs for awhile, because my then teenage friends were all into the CCG craze playing: Middle-earth the Wizards, the original Star Wars CCG, and of course Magic: the Gathering.
*I went to college for a year in Wisconsin and I wish I would have spent more time visiting places up there, but I did buy some Magic and got into Vampire: the Masquerade with some cheesehead goths. Hehe. :D
*I came back to PA, worked 2 jobs, went to community college, and got married. Being married curtailed my spending but that was probably a good thing. Haha. I joined a local gaming club and started buying used games there as well as from the vendors that set up at that club's gaming convention. Mannn... I got some great deals on the last day when vendors really didn't want to lug games back home. I bought my first copies of Empire of the Petal Throne there on the cheap from Andrew Lorince. Woohoo!
*Sometime after that DriveThruRPG became my main way to buy cheap PDFs of games, but I did pop in a local used book store now and then to see what they had on their shelves. I miss that little hole in the wall. I got some great AD&D books and box sets there.
*When I had kids of my own my spending was greatly reduced, as I had to cut back on working to raise them. I bought some PDFs, and I think I even started backing some Kickstarter projects around this time. I resisted doing that at first, but then I got addicted to backing friends' projects mostly.
*At some point I began using free sources and games for the most part, or picking up cheap retro-clones in print. I cut back on Kickstarters and eventually I just stopped backing them altogether.
*I've spent the most of my spending recently on physical games from Lulu when there are discount codes, and buying at cost physical copies of Basic Fantasy from Amazon along with some generic random chart/table books.
*My buying has also shifted to include games for my son who is 9. Basic Fantasy, Cepheus Engine/Traveller, and Fantasy Flight's Star Wars are good examples of that. He tends to like sci-fi games mostly. I often run games just for him but that may change if the local kids want to play too eventually.
How about you?