I still have my disks for Cakewalk Pro 3.01, which I had on a custom built 486DX built with a MQX-32M 2 Port PCI Midi Interface.  I use to sync it with MMC to a Roland VS840 for my audio tracks.  Great setup back in the day...around 94 I think, added the VS840 around 97 or 98 ?  It replaced my Alesis MMT-8, which had replaced an earlier Yamaha QX7...I better stop there.

I remember I had some midi sequencer software on a Commodore 64, it could have been Voyetra.  I just remember every time I wanted to do a different function (like laying down a MIDI track or editing notes) you had to swap out different floppy (and they WERE FLOPPY) discs in the drive.   One time I got so frustrated from the constant "making flippy floppy", I almost bent the disc in half. 
I still have some old 3.5" disks of MIDI stuff, but none of my 5 1/4" disks survived the many moves since I last used them.

Yeah, I'm an old guy too.

As the great Yogi Berra is rumored to have said, "The future ain't what it used to be."
 
"I'm from the future. Or you're from the past. I'm so confused."

I started with Cakewalk 5 around 1992

I picked up P8 shortly before PA9 came out.  I've had most versions along the way, although I did skip some here and there.
 
There is another one out there I like a lot, but the development for that is lacking an adult in charge to keep the devs all going the same direction.  It's mixed.  Some really cool innovations come out of it, but it's not a cohesive whole.  Great for geeks that want to tweak their environment.

I had a used Fostex 8 track that I synced with Cakewalk DOS 3 in about 1988 (if I remember correctly).
 
The SMPTE stripe I put on track number 8. It left me with 6 audio tracks because the SMPTE would bleed onto track 7. I used Cakewalk to trigger a couple of rackmount synths, I think a TX81 and a cheap Roland sampler.
 
Actually track 7 was usable but was noisy.
 
The whole thing was surprisingly reliable.
 
I would mix down onto a cassette deck.
 
I loved the tape compression, no matter how hard you drove it it sounded good.
 
I notice Sonar still has SMPTE sync capabilities.
 
......A bunch of nostalgia about the old days.
 
 

I started on Guitar tracks 2 then went to Sonar 1 and many more versions and now Sonar Platinum its been a long ride but not as long as some.
I didn't try to record back in the dos days thank goodness, I was too busy doing it live.
Must say it has come a hell of a long way!
Loving the new tools especially that new talent plug in! LOL!
Running it on 10!! cause I need it!
 

pharohoknaughty
I had a used Fostex 8 track that I synced with Cakewalk DOS 3 in about 1988 (if I remember correctly).
 
The SMPTE stripe I put on track number 8. It left me with 6 audio tracks because the SMPTE would bleed onto track 7. I used Cakewalk to trigger a couple of rackmount synths, I think a TX81 and a cheap Roland sampler.
 
Actually track 7 was usable but was noisy.
 
The whole thing was surprisingly reliable.
 
I would mix down onto a cassette deck.
 
I loved the tape compression, no matter how hard you drove it it sounded good.
 
I notice Sonar still has SMPTE sync capabilities.
 
......A bunch of nostalgia about the old days.
 
 

Ah memories! Back in the late 80s I also had a Fostex 8 and it's little brother the A2 2 track for mastering. (like I knew how to master...). The "8" was sync'ed to an Amiga 1000. My only synth was a Korg Poly 6.
 
I did not have the channel 7 noise as you talked about. When I bought the unit I measured the operating parameters including crosstalk and everything was in spec.
 
Walt

Interesting to read some of the histories.   I found this thread because I'm trying to determine how far back to downgrade from X3.    Any point of view on that?    I've used sonar producer 5 very happily, I, politely, do not like x3.   Is there a middle ground somewhere?  Especially a version that improved on sonar 5 in the midi world and was/is reasonably stable on windows 7 64 bit?