Ignoring the crap things I did as a kid with cassette recorders, basically I got into this to compose music for games I was developing as a hobby. So I started out with MODs at first, because those were the technology of the day.
Then people started to switch back to MIDI and I followed, using a free copy of Cakewalk 3 from a coverdisk. Eventually people started to use ADPCM, Ogg and MP3 and at that point it didn't matter what the underlying composition tool was because it was all an audiostream at the end of the day.
By this point (around 2002) I started to get fairly good with Cakewalk, but the sounds I had sucked, so I bought a Roland MVS-1 which was fantastically better, shortly followed by a JV1010 with orchestral module. To begin with, both of these were hooked into each other (the MVS-1 being able to take an extra input and mix it). At this point I was recording straight from the sequencer into GoldWave.
Then I went out and bought a Behringer MX802a mixer, and began using that instead. I bought a few more synthesizers and some outboard gear and my compositions were getting sufficiently complex that the sequencer (now Cakewalk Home) was starting to buckle under the weight of all the MIDI tracks and would screw the timing up, so I realised that I needed to invest in a multitrack machine.
Before I did that I went slightly insane and bought a Tascam 32 which I would record to first, before dumping things back into Goldwave for use in the game. In 2003, the price of a digital 8-track was pretty much on par with an analog one, so I bought
a Fostex A8.
It had a number of problems and fixing it would have cost more than it was worth. In fact I still have it boxed up downstairs, since I'm reluctant to see it parted out by someone, even though it doesn't really work very well.
Anyway, about this time people were starting to comment about the music and I realised that it was getting good enough to stand on its own merits rather than as background music. I began idly to think of recording songs, but it wasn't until I saw the 'Dark Side of the Moon' DVD and heard Roger Waters sing with no effects or accompaniment that I realised my voice was probably good enough.
I then purchased a TSR-8. The difference in sound quality was like night and day, and it is still the centrepiece of my studio. Everything is still done in MIDI, with Cakewalk SONAR and laid down track by track onto tape using a timecode on the multitrack to sync everything and mixed down to a Revox B77HS at 15ips. I usually use Rosegarden for the actual MIDI playback for the recordings, but the composition is still done in SONAR.
When I have a 2-track mixdown tape, I then digitize it at 24/96 and send it for mastering.