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Until recently I've always been in the position of needing to sell something to buy a new one. Generally 'upgrading' as I go, I only had 3 electrics at any one time. (more than enough, main one, backup and athat was swapped and changed - gigged but then let go as it was no better than the original 2)
About 4 years ago I joined a busy band so started to put some of the gig money aside and occasionally treat myself. Working up to a Gretsch Setzer sig (gorgeous guitar). After a couple of months gigging this I started to get twitchy in certain pubs, so reverted to the original 2 for these gigs. Realised I was playing the Gretsch less and less so I sold it. The guy who took it p/x'd a nice PRS that I (foolishly) sold. The PRS sale was also a P/X but this gave me a bit of cash to use if I saw any bargains.
Some have come and gone and others have come and stayed to the point where I now have 9 electrics. I've gigged them all recently but still find I'm using 3 more than the rest so decided on a cull. I've just done a deal with @CasperCaster that has seen an old amp of mine come back home and a very nice Strat go his way.
The long and short of this ramble is that over the last 2 years I have gone through over a dozen guitars (plus the ones I still have), enjoyed all of them for a while and considered it a long loan period for those that have gone or are going.
It's been fun, I've gigged guitars that I'd never have usually considered, but it's been a useful exercise.
I'll be happy when I'm down to 4 electrics, especially as I still have a hankering for a nice acoustic.