I did.  
 
I started with a 2 track reel-to-reel.  I upgraded to a 4-track. Then a Tascam 8 track cassette with integrated mixer.  Then an ADAT. Then another and another (24 channels of ADAT+ BRC) driven by a 24*2*8 mackie analog console (as long as a battleship!).  At some point, I think the BRC provided sync to Cakewalk or vice versa when Cake was MIDI.
 
I started retiring the ADATs as Cakewalk Pro Audio became a more viable option (slowly at first).  I think my ADATs are now snapper reefs somewhere.  
 
I wonder how many folks out here are so young they never saw tape?
 
 
 
 

My first system was a Tascam 688. I had a 486DX4 100mhz with 1 mb of ram. I had it synced with Cakewalk 1.0 for Windows 3.1 using a board that had 2 sets of MIDI IO and SMPTE. I don't know if I ever fully mastered that 688.

Tape? We scratched cave walls with a sharp stick!
 
OK, I'm not THAT old. First tape recorder was a little 1/4" R-R, using the microphone that came with it. I'd set the mic on a pillow on a chair out front of the band. That was c. 1965. I didn't get a proper deck until 1975 - a 15 ips TEAC 3340S plus a 7.5 ips Pioneer R-R to mix down to. Of course, everything ultimately ended up on cassette. So yeah, there was some tape involved, for sure.
 
Cakewalk 1.0 (1986?) was basically a way to save tracks and reduce the number of bounces.

First system was the 4 track Tascam in the mid 80s. In the late 80s/early 90s I got the 8 track Tascam cassette and used a synch tap with it to hook into my 80/86 desktop which powered my dos midi software called cakewalk version 1 if I recall. It controlled my Roland d110 rack module and my alesis dm4 drum rack module. Think i was using an ADA guitar preamp for the guitars. Then sold it late 90s cause I saw the direction we were heading too. 2004 went full digital and used a bunch of effect racks to add reverb n stuff. Had/have the line 6 pro racks for guitar n bass and upgraded my drums to the Alesis dm5. 2016 ditched all racks and using virtual drums, virtual keyboards and simulators for guitars.

My first system was a Fostex 8 track recording onto hard disc.
 
I then invested in a 2nd machine and slaved them together using Midi Machine Code to sync them up.
 
The largest size of disc that the Fostex OS would handle was 4.3Gb

Fostex 4 track cassette here. I used one track to sync pre and early MIDI Roland sequencers.

I had an interesting evening in the early 70s visiting Dartington School of Arts music department watching massive tape loops strung around microphone stands, the then bleeding edge of sonic experimentation.

Hi Maurice!  Good to see you back in the Coffee House!  (Are you taking good care of "my" guitar?  )
 
4-Track Tascam in mid-80's for me as well.
 
Hmm...  I wonder what happened to all that stuff???
 
 

A Yamaha  4 track ,MT ? in the 80,s.
Who could at this times imagine to run
a complete studio in a pc  for under 1000 bucks ?

I started on a VestaFire 4 (I believe it was called), in the 90's.
In the end, only 3 of the 4 tracks worked.. Even then it was fun 

TEAC 4-track Reel and mixer.