I bought my first guitar in 1995, the year after I left school. It was a Samick Les Paul type guitar that looked like this:

and I played it through a Starfire 20w amp that looked like this:
Sometime during 1996, I decided I wanted a proper Les Paul, so I went off to a little shop in Pietermaritzburg called Babs Music and the owner, a really great guy called Babs Naidoo ordered me a Black Gibson Les Paul studio and allowed to me to put it on a 6 month Laybye. The guitar cost R5k and at the time I earned R1300 per month, and so every month I went to his shop and handed him most of my paycheck. After about 3 months he must have felt sorry for me, because he went and fetched the guitar out the back and let me take it home, even though it wasn't even half paid off, and let me continue to pay it off without an ounce of collatoral.
When I finished paying the guitar off, I bought a secondhand Marshall 8080 Valvestate amp, that I had from 1996 and gigged with regularly from 1998-2001. During this time I also owned a couple of other guitars, like an Epi Les Paul gold top that I used as a backup for a while and a Fender 60's reissue Strat with aged hardware and plastics, and a rosewood fretboard, both of which I sold. I also had a Rickenbacker 4003 bass that I also sold in around 2003 or so.
I took a long hiatus from guitar and music in general until around 2008 when I got the urge to play again. I decided it was time for a nice valve amp, and got myself a Marshal JCM2000 TSL 60W combo that I did a few gigs with before my first son was born in 2008.
After admiring the Gibson Historics for a number of years, but puking a little in my mouth when I saw the cost, I stumbled on a guitar at Route 66 Classic Guitars in St Louis, Missouri, that had something special about it. I'm not really sure what happened after that, but somehow the planets aligned and a few days later a 2010 model 1959 Reissue was in my hands.
A month later, after following the Marshall AFD100 development project on the web, and drooling over this amp, which for a big fan of Slash like me, was my ultimate amp, I was surprised to find out that despite it being a limited edition of only 2300 amps worldwide, and before the USA had even seen their consignment in the flesh, and with only a handful of UK guys having taken delivery of their preordered amps, there were already 2 sitting at a shop in Durban!
I headed down there one afternoon, guitar in hand, and after a couple of hours, came home with an AFD100. 4x12 Marshall cab and a big hole in my wallet.
Decided to get rid of the TSL last November as wasn't getting much use after the AFD arrived and eventually I decided to trade it in on a vintage 4x12 Marshall cab and a JMP head. Both were in really poor condition, but since I like to get my hands dirty, decided that they would make a fun restoration project and in the process I might learn something.