I honestly buy more pedals than anything else, but guitars have been weird for me.
Got a squier strat as my first guitar. I loved it but slowly grew to hate it. Didn't like the single coils, didn't like the look, felt too "mainstream" of a guitar. I mean, everyone played a strat, right?
My next guitar was a Cherry Red Hamer Echotone. Saw it during The List Sale at Guitar Center (years ago when it was actually a sale worth going to). My dad and I would take trips to our local GC often. I fell in love with it and gave my dad puppy dog eyes while he negotiated the price with an employee.
After that I was on a Hamer high and got a beautiful orange sunburst Hamer Standard (Explorer body). That guitar didn't last long, as I ended up trading it to up my amplifier game. I do miss it.
Next one was a custom guitar I bought during high school with money from work. I was in a huge Jerry Garcia phase and worked with a relatively no-name luthier to make a Wolf/Tiger/Les Paul/Strat bastard. Beautiful wood and sound, ugly design. But I love it.
After that I got a Languedoc clone - Trey overtook my Jerry phase. Also worth mentioning, during that time I was on a reprise SRV binge which resulted in my current Fender Vibratone speaker.
And over the years, my tastes changed, and I found myself wanting a Stratocaster again. I did want a Les Paul at one point, but decided my dad's SG and my Echotone filled the role well enough. My custom guitar and Ollangdoc had spilt-coil humbuckers, and I found myself using the single coils more and more often.
As I was there at the counter buying my 2015 Olympic White Stratocaster with my dad at the old local GC we used to visit, he reminded me years back when I told him I never wanted to play a strat again. I remembered; everyone played a strat, but now I know there's a good reason behind it.