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"Take these three items, some WD-40, a vise grip, and a roll of duct tape. Any man worth his salt can fix almost any problem with this stuff alone." - Walt Kowalski
"Only two things are infinite - the universe, and human stupidity. And I'm not sure about the universe." - Albert Einstein
1 was originally new then sold then a duplicate of the same run bought used a few months later, so almost bought new but not really.
In ~20 years I think I've had ~40 guitars in total. Of those, about 10 were bought new, I think.
I don't keep count but I've probably bought and sold a hundred or more second hand.
Amps - probably more like 60-40 new as I like warranties on powered things.
I’m so bored I might as well be listening to Pink Floyd
I bought one used bass from a guy about 7 years ago and it did not meet the condition he was selling it as. It did put me off I must admit. I sold that bass and luckily didn't lose any money (with the correct condition description).
I wouldn't pay the current new prices though. Especially Gibson. I always wait for stock blowouts when it's obvious a manufacturer has sold a large batch of new guitars to make room for a new model. In that sense I often pay the used price anyway.
Over the last decade I've mostly bough new (apart from a couple of out-of-production models that I wanted). Until recently it was possible to pick up clearance bargains - especially Gibsons, often with 40 to 50% off RRP. Given that popular Gibsons tend to only lose around 35% (and some actually go up after being discontinued), I was buying and often selling with a small profit. I always assumed the buyers never looked at new gear and thus had no idea how cheap they were on blow out.
Currently, all the guitars I own were bought new or made to order. I like shiny, and I don't mind any dents or scratches I might put on them either. I really don't see the point of buying used/relic'd just to have someone else's dents and scratches.
Obviously, secondhand is cheaper but, for me, I need to know it hasn't been mistreated. It probably hasn't that's just me
However for amps and pedals (at my low end of the market) new makes much more sense as often I've bought second hand stuff that has been tinkered with and not declared, or has faults or problems that aren't shared, but for the money and hassle it takes to negotiate a return (and the inevitable accusations of foul play that get thrown around when you dare to criticise an item) it's just better to buy new and buy well
1 you get more bang for your buck 2nd hand
2 I like a nicely played in guitar waaaay more than a stiff new thing
3 I don't like shiny blingy guitars - I worry about damaging them
4 I actively like tatty old aged guitars
5 I like to dismantle guitars, mod them, faff around generally. I don't do that with expensive new guitars.
So secondhand for the win.
I do like the idea of buying used because it's so much better value (especially if I ever sell it on) but a couple of things hold me back, it's not that I actually care about having a brand new guitar.
Firstly there's a lot of dishonest people around so I could buy a used guitar, only find a big problem with it a week later but never hear from the guy again. With a shop I can always go back and they'll definitely do something about it (would buy used from a shop).
Probably the main thing that's stopped me, though, is that any time I find a guitar I've wanted it's rarely on sale second-hand at the time.
Can only guess that those who mostly buy used guitars are either not looking for a specific model/finish and are just browsing what's on offer to see what takes their fancy or if they do want something specific they check for it regularly and patiently await it coming up.