I have been through all of that over the years.
I love trying out new instruments and when I was young I couldn't afford an expensive guitar, it took a lot of hard work on behalf of my parents to afford my first electric guitar, a Vox Duotone and a Watkins Dominator amp. After that I took over the payments on a Fender Stratocaster in PX for my Vox guitar and it was a struggle to pay but mum & dad helped again. Like many, I had to settle for a Watkins Copicat rather than a Binson or Echholette and never had the chance to play the more 'upmarket' kit that seemed to be the requirement.
It's because of those memories that I now buy and sell stuff at the rate that i do, because I can. I have had and in some cases still have some very expensive desirable guitars, some which were beautiful instruments but weren't for me because if comfort issues when being used on stage. By and large I have broke even with purchases and sales, so to me that's fine and it has given me the opportunity to own and play very desirable instruments.
What I do enjoy is finding new budget priced instruments that compete with the elite, I'm currently into the new D'Angelico range of instruments and they are superb as well as being very reasonably priced. I'm also a big admirer of Alan Entwistle and Trevor Wilkinson for their excellent products, the Vintage guitars are great value and good working guitars. Of course I still love the Fender Strat, Tele, Jazz, Jag etc but each guitar gives something different and I enjoy using all of them for different things.
As I've mentioned before, I prefer my Burns SSJ to the Marvin - probably because of it's similarity to Strat in the trem department.
I seem to play differently on a Les Paul or a Gretsch to the way I play my Stratocaster, but people still tell me it sounds like me. One of my favourite guitars is my Brian May which is so versatile it will comfortably go from the soaring Queen sound to Hank Marvin at the flick of the switches and it is so easy to play.
I have a special affection too for the big archtop guitars that are associated with jazz, but my interest is the connection they have with rock & roll, Scotty Moore, Carl Perkins, Chet Atkins etc. I've owned a few of them but I can't feel comfy with them on stage so I always let them go. I have a couple of Epiphone 339s that are small bodied 335 types and they are great for stage work.I recently picked up a D'Angelico 335 and that's quite comfortable on stage and as I got it second hand, didn't cost a fortune, I like those kind of guitars.
I'm selling stuff that I bought and don't use, so in effect financially, I remain on an even footing and eventually when I've tried and tested everything out there, I will prune down the collection to something sensible and keep guitars that I know I will use and enjoy. Some people collect paintings and art, some collect expensive jewellery and watches but I have no interest in that stuff, the important thing is that the guitars and echoes & amps & effects keep me busy and out of trouble, whilst allowing me to offer experience and advice to those who ask.