My first Mac was a Mac SE. I had an Apple IIe and IIgs before the Mac. The IIgs had some GUI sorta like Mac lite but the reason I changed from Apple II to Mac was Hypercard. I saw it at a MacWorld Expo and I was hooked. I WANTED to make Hypercard databases so much and I did for years and years. I loved that Mac and have had nothing else since. I think the Mac cost about $4000.
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I was a longtime Windows user but after playing with Linux in the late 90’s and then discovering OSX while supporting some Max’s at a job, figured I’d found the holy grail. Bought a 2003 PowerBook and never looked back! That machine could still start up a few years ago, but no surprise. My 1992 Powerbook 180 still works fine!!
My first Mac was a Mac SE FDHD, though it wasn’t mine I was the tech support for it (I remember putting in the 100MB drive to upgrade the internal).
I had an Apple //e (upgraded from a ][+) and a //gs with FOUR MEGABYTES OF RAM! before I switched to the Mac. In fact, I still had that //gs until late 2012.
I bought my first Mac last year, so what?
My first computer I build myself in 1980. A CPM machine and I had to change the “operating system” to the choice of my hardware. Soon to be followed up with some IBM clone PC’s with PC-DOS. Went through all DOS versions OS2 and I even tested some multi user operating systems that never were a great success, but I needed them for testing software I was developing for multi user access. Got through almost every Windows version, except Vista and 8.
After I retired, my hobby photography became more and more important and I wanted to use my computer, without fuss. A few years ago I could use an old MacBook Pro 17 inch from my son. It was much faster with Photoshop, than a newer PC with almost the same hardware and Windows 7.
The thing that drove me to Apple, I almost never had to wait when it needed an update. And never a problem while updating.
It took me a couple of years to put aside enough money for a new iMac 2017. This machine does everything I want and is so fast, my productivity with Photoshop is not doubled it is now 10 to 20 times as fast.
In my years as a technician, it was great to play around with hardware and software. Believe me I could solve (almost) any problem. The mostly self build computers were great and could be used. But if you need a computer to work for you the only choice can be an Apple.
I don’t need to play admin like in my Windows years.
For my music collection I use CATraxx and there is (still) no replacement for MacOS. So I installed Windows10 with Bootcamp. The few times I use this program I most of the time have to wait, because Windows wants to install an update first. It only makes my aversion towards Windows greater.
My first Apple computer was the PowerBook Duo 230, bought in 1993…
It was for my studies.
My favorite app at that time: Syndicate. What a game! 
I’m actually a former Microsoft employee as well as Windows enthusiast.
But after having been on the iPhone train for years, I finally decided to make the switch from Windows to Mac OS X (good ol’ Snow Leopard) back in 2010.
At the time I didn’t really know much about the performance of Macs, and were still convinced that laptops were a waste of time and money, so I bought a refurbished quad core Mac Pro 3.1 thinking that this machine would probably live up to my expectations which it did, and then some.
Upon booting up for the first time I was blown away at the speed of this machine which were miles ahead of my previous Windows machine (which wasn’t a slow mover, either). And the speed at which I could process both photo and video on this machine didn’t leave much room for improvement.
The only thing I missed a bit back then, was the ability to run games on it, but eventually I figured that out as well.
As time went on, and I went back to school, I finally buckled and bought a MacBook Air late 2013, crossing my fingers I wouldn’t regret it - which I didn’t, so I ended up selling my Mac Pro, even though with a heavy heart, but I just didn’t get around to using it any longer, so I figured it’d be better for it to be used than collect dust in my home office.
I still use my MacBook Air, and even though I (regrettably) only have the 128 Gb SSD + 4 Gb memory model, it still gets the job done, wether I am working in Photoshop, or Final Cut Pro.
So, all in all, I am very happy having made the switch 
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My wife won an Apple ][e when we were in grad school which we later sold to buy a used Mac Plus… back when that was about the latest Mac.
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My first Mac was an SE 2/20 yep 2 meg of ram and a 20 mb hard disk.
That was back in 1989.
I bought it mainly because of Adobe Illustrator 88, And some vinyl cutting software that enabled me along with a (still working) Summer Graphics cutter plotter and adobe type manager to actually (see) the fonts, unlike anything else on the market at the time. I now run the plotter off a PowerBook 1400 that was my first laptop. I still use this setup every week at work to cut out vinyl for current jobs and it’s perfect. The SE did work a few years ago when I tried it again. It still has pride of place on display in my office but I haven’t tried firing it up recently. This first fab setup got me well and truly into the Mac.
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The first Mac I ever possessed and used exclusively as my own, even though it belonged to my employer, was a Titanium PowerBook G4. I worked in a group that managed the computer labs at a university, and we lost our graduate student who managed the Macs in our labs. Even though I was, at the time, very anti-Mac, I volunteered to take over the responsibility for managing our Macs, but requested a Mac laptop so that I could immerse myself in the operating system and ecosystem. I figured I’d have to do this for a semester or two until we could find a new grad student, but, to my surprise, I fell in love with the Mac. I started using my Mac laptop as my primary PC, and the next time we purchased desktop Macs for the labs, I got an extra for myself - a G5 cheese grater.
My very first personally-owned Mac was 24 inch 2009 iMac that is still in use at my parents’ house.
Since switching to the Mac in the early 2000’s, I’ve converted many in my family, friends, and all of our church staff to the Mac. 
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My first Mac was a 2007 iMac, quickly followed by a 2008 15" MBP and a 2009 MacMini.
The iMac and MacMini are both still going strong, but now have SSDs installed but they can now no longer run the latest OS’s. My 2008 MacBook Pro failed just as the 2016 MBP’s came out so I did replace that one with a Touch Bar MBP 
but I really don’t like the USB-C only ports and the need for a bag of dongles and I never use the Touch Bar.
I’ve always preferred desktops to laptops but sadly there isn’t a Mac I would buy at the moment so I’ve recently purchased a second hand 2012 Mac Mini as my main machine and upgraded the HDD to a larger SSD as well as maxing out the ram. I’m not sure whats going on at Apple but the current MacMini and iMac line up is a joke. I went with the 2012 MacMini as I could upgrade the ram and HDD, but I won’t be spending money on a non upgradable desktop, HDD’s will always fail and ram will need upgrading but I doubt Apple are going to allow us to upgrade these parts in the future :(. So I’m seriously considering going back to Windows if the Mac’s don’t improve over the next year or so.
My first Mac was a 512 I bought with the earnings of my first summer job + a year’s worth of babysitting money. I loved it so much I kept it in a closet until 2012.
Also, even now when I boot up, part of me expects my machines to say “hello” and smile.
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Oh dear, I guess I am outing myself as a really, really old man here … 
My first Mac was a (gasp) PowerBook 180.
A heavy grey brick with a trackball and a surprisingly good “active display” with (gasp again) 16 shades of grey.
I basically had to get a Mac since my PhD supervisor (hey there, Lisa) was leading a Macs-only lab at that time (1994). And probably still does.
My favourite app turned out the Infocom version of “Hitchhiker’s Guide to the Galaxy”. Which was fine with 16 shades of grey.
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My first Mac was/is a 2017 (at least that’s the year I purchased it–I’m really really new at this) MacBook Air. The moment I got home and turned it on and began using it I fell in love. It suddenly made sense why this was the way to go.
I’ve been a Windows/PC user since my first computer (1996 Compaq). But without wanting an iPhone, I went in to my AT&T store in 2009 and got my first iPhone (3G). Years later, I bought an iPad Air (1st gen) off a friend. Then an Apple TV (3rd gen). During this slow accretion of Apple products I went through 3 desktop Windows PCs and 3 Windows laptops (a few Dells, a Gateway, a couple of Compaqs). I was tired of going through computers/laptops every few years.
And all along I had friends, Mac users all, who kept telling me “Get a Mac.” So, I did (it busted my budget). I will never go back. Of course, everything syncs and hands off, and what not. But the word I felt described my initial moments with my MacBook Air, holds true still: it was the most elegant computer experience I had ever had.
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The original Macintosh. 128k. Got me through law school! I loved that little box. Have run macs ever since except for a couple of years where I had to use PC for legal software.
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2008 Aluminum Unibody MacBook. I had gone through three windows laptops in four years and the last one died right before Steve Jobs announced the unibody MacBook. It was far and away the most advanced laptop you could reasonably buy at the time and I picked one up a few days after it was released. I never looked back.
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My first Mac was a 2007 MBP. At this time I was a die hard windows user that had got fed up with PCs so I decided to buy a used MBP to solely run Windows in Bootcamp. Eventually, curiosity got the best of me and I started playing around on the Mac side and was eventually one over because of Hot Corners and Spaces. Now, I’m a die hard Apple fan and can’t imagine ever going back to Windows
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I upgraded to an Apple IIe from a TI-99. Used that for a couple years and then went to a PC with a 40MB (yes, megabyte) HD. That was an upgrade from the standard 30MB and I thought I’d never need any more storage than that. HA! Went back to Mac in 2006 and never looked back.
My first Mac was a 2008 MacBook Pro. I really wanted one of those black MacBooks, but I was convinced that I needed a “Pro” model for my music production. I used that machine every day until mid-2012, and it even survived the Great Sweet Tea Spill of 2009.
It was also the first Mac that I ever had the chance of tearing down, since the sugar from the sweet tea crystallized and locked up my fans. Somedays, I really miss that behemoth.
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The RAM will stay regrettable but you can easily change the SSD for a bigger one - check out MacSales (OWC).
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