I remember a time where an ambitious young teenager was increadibly excited about guitar. I remember when he had metal streaming through his veins and loved him some chugga chugga. He liked to frequent guitar center often. Not to play or "show his chops" by turning the line 6 spiders up to 12 on INSANE mode and wanking in front of soccer moms and hip dads but to oggle at the many different peices of beauty on the walls and floors.
The the adversary, stan himself (actually it was John from guitar center but same difference) appeared and said "LOOK AT TEH POINTZ ON DIS B.C.RICH!!!11!! ITZ TEH BR00TZ!! JAYMZ HETFIELD PLAYED DIS MODAL!".
So guess what mum got me.
What was I thinking?

That was part 1.

Part 2 is roughly a year later. (BTW at this point I'm playing out of an acoustic bass amp and a metalzone. Br00tz).
I was at the guitar center again and had a year to fully absorb why the low end BC Rich models aren't so good. I was browsing and playing on different guitars that were somewhat within my price range. I came across a Schecter Damien FR. It was probably the best guitar I had ever played. Action was soo low (compared to the Avenge) and it just felt very nice in my hands.
If I remember correctly I went halves with my mom to get it and it is the guitar I have had to this day. I still don't think it's a bad guitar but looking back I really wish I knew what I know now. I would have been able to make an informed decision. I currently hate playing on it and am saving to get a decent high quality instrument.

I believe one of the reasons I don't like this guitar anymore is that my tastes (asthetically and Musically) have changed so drastically.
Another reason may be that I am not longer a teenaged highschool kid? Maturity kicked in or something like that.

TL;DR: The point I'm getting at (there was one when I started this but I think it's changed a few times) is has anyone else bought gear or made decisions they regret as far as instruments? Why do you think you made these choices in the first place? What have you done to avoid making similar decisions in hindsight?

Sorry if this is an incoherent wall of text. It's 2 a.m. where I am and I have had a long day.
Two things I've regretted:

Paying £80 for an OLP EVH neck. It was dirty, frets were worn, I totally forgot to check if it had a floyd nut slot, it didn't fit in the OLP body I had previously bought. It was a lot of work to make it useable.

Paying something similar for an OLP EVH body. The pickups were horrendous and screwed straight into the wood but ridiculously high and the threads for the floyd pivot points looked like they'd been hammered into the body, one was actually under the surface of the wood.
When altitude dropping, my ears started popping. One more red nightmare...
I bought a Boss DS-1 when I still had my small fender practise amp.

I kinda regret selling my acoustic guitar last summer too. Must get another one.
i've purchased two guitars in my life and i've regretted one and been mostly happy with the other.

The first acoustic i purchased was just far too early in my acoustic career to make an informed decision. i bought it without doing any research, and made the decision in a hurry.

The second acoustic i bought was a year later, after playing some friends' guitars and researching a bit more about what i'd like in a guitar. i also played everything in the shop, some very nice ones that were far beyond my range to get a feel for what a really good guitar felt like. However, as the years have passed, i've found that this guitar has a few notes (F# and to a lesser extent, F) that resonate strangely with the body, and a couple other little quirks.

But all in all, i think it's part of the learning experience with playing an instrument. In retro-spect, i definitely could have improved the process in which i bought the first guitar, but i'm generally happy with the second one.

And i now i'm looking into going to electric guitar, and i can only imagine what kind of surprises i'll run into when as i play and buy them
oh loads of stuff, a dean 7 string, a bunch of cheapo amps, the classic mt-2 mistake, a schecter , and some little things (strings etc)

But you learn from mistakes, and now i've got gear i'm happy with. I can build on it more, but what i have at the moment is great fun and sounds like 'me'.
Upgraded HSS USA Fender American Series Strat
G&L USA 30th Anniversary Legacy
Laney Lionheart 20 112
Generic Boss DD-3
Blackstar Ht-1
and an old Beaten up dunlop Mr.Crybaby.

I don't regret any of my guitar buying decisions. I've found, like everything else in life, you have good times and bad times with guitars and gear. When it's new and shiny all is well, but once the honeymoon period is over, you start getting acquainted with the limitations of the gear. My Jackson is a one trick pony. It does heavy music really well but that's it. The Live Wires are not versatile pick-ups and the FR is worn and in dire need of replacing. Yet I still love it to bits. I went off it when I got my Mockingbird and didn't touch my Jackson for nearly. Then I found that I got bored of the cleaner tone of my Mockingbird and annoyed at feedback issues at gig volume. I'm now using my Jackson as my first guitar and loving every second of it. However, I expect to be using my BC Rich again within another year. Probably with heavier pick-ups installed.
EVH Wolfgang Special LH
Gibson Les Paul Studio 2013


Fender Hot Rod DeVille 410
Laney IRT Studio + 112 cab
nothing new here. many first time guitar buyers buy a guitar because it looks cool or is similar to what their fav player uses. sometimes this isn't the right choice for you as a player. normal noob thing to do. as you learn to play or get older you often will expand your musical horizons and change direction that to is normal. when i first started to play (late 70s) i was into the metal of the time and of course after eddie hit was all into the shred thing as well. took a while but i discovered that although having some speed is a good thing that i really wasn't a shred player. i also wasn't the best thrash metal player either. once i started to go with my strengths (but still do work on my weakness) i became a much happier and better player. it's all a journey and you just have to learn along the way.
I regret having to return my Charvel San Dimas because the transmission dropped out in my car the week after I got it. That guitar was so tasty.
I always regret my purchases, and then realize later on that nothing else would have worked better for me, so I become happy and stay happy with them.