I've bought and sold a ridiculous number of guitars over the years. In the past few years I have been making a conscious effort to buy only guitars I want to keep and keep the good ones. This has become possible because I have gradually worked out what it is I actually like/want. And because Gretsch finally made the guitars which sound like the magic "Guitar In My Head". I have a couple of guitars which are purely about the sound - although they look pretty cool too (Gretsch Duo Jets). Then I have a couple which are my "dream guitars", ie guitars I always wanted and would regret selling (Gretsch 6120, brand new USA Epiphone Casino), and then there's my "ultimate blues/roots guitar " which would be very difficult to replace (Gibson ES-225RI from a coupla years ago). I'm at a stage where I really do have everything I want.
Some of this has been financed by building amps and pedals, so it has worked out pretty well. I always build amps for me, but then I have too many and need to sell some to make space. I figure if I sell my favourite amp (which I have done a few times) I can just build it again, maybe even better. Same with pedals. And the best thing about building amps and pedals is that you can seriously tweak things to suit your style. I have got my amps to the point where I would struggle to use most commercially available amps. My own builds work so much better for me. Same with OD pedals. I have got to a point where I have my own OD pedals built for specific sounds which suit me. And often it turns out they suit other players too. Selling amps and pedals paid for my brand new USA Epiphone Casino, and I'm pretty happy about that!