If You Could Get Back What You Paid...

Voxman

Unfortunately, until more recent years, Ive not been in a position to buy new and not be concerned about losing money if I had to sell.

It may sound a bit sad to purists, but Ive therefore had to buy guitars with my head as well as my heart. I would make money on every guitar I've bought in real terms if I decided to sell (which I don't want to). That's because I've only bought pre-owned and not new and won't be tempted to pay silly money for something. 

I was very tempted to buy a brand new Fender Vintera Telecaster 72 with the dual humbuckers a few months back but dithered too long and the price shot up to (in my view) an unrealistic level. 

My approach has meant that over the years I've been able to buy some very nice guitars and have a collection that has grown in value and covers all the guitars I like.  So very similar to @Pabcrane I've been very fortunate with the guitars I've bought which have all been goodies and I've kept because I enjoy playing them. But if I did ever buy one that didn't suit, I would sell it, not least because I'm struggling on space. 

I don't actually need anything else now....but I might make an exception and treat myself to something a bit special as a retirement present to myself. Haven't decided yet, but it's likely to be either a Custom Shop Strat, a Les Paul R8 or R9, or a Feline Lion.   

I would sell some of my amps now simply because these just aren't getting used as nowadays I use modelling fx for gigging straight through the main FOH board.

Keefy

I’m pretty happy with my guitars and basses at the moment.

Last night when I was waiting in vain to fall asleep I realised I had barely touched one particular guitar in several years, so I decided I’d sell it. This morning I got it out to dust (seriously!), plugged it in, and realised I had forgotten how nice it was. In the meantime I had checked its value and found it is worth about what I paid for it new 12 years ago!

It’s staying for the moment, at least until I can take it to an open mic, but it may yet fall victim to Jazzmaster GAS. Which brings me to my point - it’s always been a new guitar that has caused me to re-assess whether I regard one that I already own as an instrument to enjoy playing, or as a source of funds.