Sometimes waiting to buy something isn't a good idea as you'll only end up paying MORE later. I recently caved and bought a brand new Wii U Pro Controller and it cost me over $100. You might be going "why the fuck did you buy it for that price?" I guess it's just genuine FOMO kicking in big time, I'm trying to buy up pretty much whatever I can for my Wii U before Nintendo's support for the console ends entirely in March (I also have trust issues with used/refurbished gaming items, so sure a refurbished Wii U Pro controller would have cost less than $50 but then I'd have a worry of "what if the thing comes in and some of the buttons don't work right due to a botched repair?").
Also I missed out on some games back when they were new and I look back and wonder why I didn't get them back when I had the chance. For example I missed out on Mario Kart: Double Dash back in the day and I genuinely don't know why I did despite Mario Kart being a series I've always enjoyed, and given how often I see people still sing its praises as maybe the best game in the series I sometimes then worry "since I didn't play it when it was new, if I have no nostalgia associated with it will I feel the same way or be let down by hype?" (one infamous example of mine is I didn't play Morrorwind until after playing Oblivion and Skyrim, and after seeing all the praise people heap on it I went into Morrorwind with high hopes, and I came away going "dude I just don't see the hype…" as some aspects of the game feel needlessly clunky, I hate how slow your starting movement speed is unless you pick VERY specific traits early on, and combat felt too unresponsive for my liking).