Started in 1987 with a Tascam Porta 05(still got it :))
Then got a Tascam Porta 564 4 track mini disc recorder in the mid 90s
In '98 I got my first computer system running Vegas Audio 1a with an Aardvark Audio Aark 20/20 interface
Then updated to Sonar PE 6 in '05 with a Delta 1010 rackmount interface
Now I'm running Sonar Platinum with an Audient iD22 interface
(There have been computer changes over the years too)

Great idea for a thread. And hilarious that I can copy and paste from most of the pictures above to show my first two as well.  I bought the Sony r-r as part of our home stereo system and only recorded a few things of me playing. I was disappointed that it didn't do sound on sound without a 250 ms delay.  
 
The Yamaha 4 track was I guess my first serious machine. I had borrowed a Tascam Porta studio before that. I bought the Yamaha because it was one of the few that could do all 4 tracks at a time.It used a weird noise reduction that resulted in artifacts on female vocals. 
 
Then that picture above of the Tascam midi studio 8 track, not sure if that was the exact model, but I rented something like that in the mid 80's and a Tascam 2 track reel to reel to do an album of Russian kids songs. It was my first 8 track recording and yes we used track 8 to sync up my Atari running KCS and a Roland MT 32 and GR 50 for sounds. I had to keep renting the 2 track so I bought it out in the end. 
 

 

 

1. Fostex B-16 Reel to Reel - given to me by a trust fund kid that was trying to learn how to record. He never could get the cables right. Took me 15 minutes to get it hooked up and going - took that long mainly because the cables were tangled. And it was FREE!
2. Fostex XR-7 4 track cassette - made traveling with it and set up much easier. Then I added a Boss DR-660 drum machine and it helped me beef up my chops because it was my metronome.
3. Fostex VF160 16 track digital stand alone recorder - opened up an entire new world of recording for me.
4. Then in February 2016, I made the jump to Sonar SPLAT.
All of my Fostexs still work too - just need to get the pots cleaned out to stop pops and crackles when turning some of the knobs. Hell, I still have my Commodore 64 with every game they made for it and it still works too.
Told you guys I am an old fart!


Al

My first recording experiences were in pro studios. In the early 80's I had a bandmate/roommate that had a Tascam portastudio that we recorded on. Right around Y2k I met a guy in Denver that had a computer with an old Cakewalk version on it. I was smitten and went out and bought a Roland Studio Pack and Sonar when Mars music was having a going out of business sale.
 
Rocky

My first recording set up was a BR-600 to record and Guitar Tracks 3 to mix back in 2007.  I was actually able to mix with on-board sound pretty well back then on a DIY PC (not necessarily built for audio).

The first real recordings that I was involved with were back in the early 80's using a friends 4 Track real to real. Earlier than that, I would use a series of tape decks and bounce between them.

My first digital recorder was a Boss 532. Then I moved into Sonar.

I had two cassette decks for duping dead tapes. I would record a rhythm on one, play it back and bring in the new sound using splitters for overdubing, recording on the second.

Old55
This may qualify as "serious", but here goes.

I had an old Grundig reel to reel in the late '70s. It was stereo and had sound with sound. It also had the green "eye" tube that acted like a VU meter. I bought it used and used it for five years. Can't remember why, I had to leave it behind when I moved to California in '83. Around '93, I had an opportunity to return for a visit and bring along an ADAT. After 10+ years, the Grundig worked like a charm. I was able to transfer a bunch of old tapes to digital. I've been "remixing" some of the tunes in Sonar.

Can't believe I'm reading this.
In my mid teens (1968 or so) my folks owned a Grundig 3 in one comprising Radio, record player and this same or very similar tape deck. Ours could be used as a 4 track with sound on sound or stereo.