For me, it was a total case of I missed the boat. I came to Amiga long after Commodore went under because I wanted to play older games (specifically SpaceQuest, Kings Quest, Lemmings, etc) and was trying to decide whether to seek out the MS DOS versions of the games and build up a Pentium (I) box with DOS 6.22 on it or to finally realize my dream of owning an Amiga.
Now, 3 years after deciding to obtain an Amiga, I am hooked! I remember very well wanting one in 1991 but seeing them go out before I could afford one. Now my A4000 is being built and I do have a full working A2000, if it had AGA, it would be the computer of choice, but I have mainly decided to build the 4000 and sell the 2000 as soon as I get the 4000 built.
This one decision actually has lead me to start collecting Retro Computers... for the same reasons, to play the old games that I have not seen new commercially developed counterparts developed -- and even if they did develop a brand new spin on the old series, I don't think the games are even close today. It's more about how pretty they look than how challenging they are (my humble opinion and yes I know there are exceptions).
So it will end out that I will have a Commodore 64, An Amiga 4000, An Apple //e and Apple //gs and hopefully an Atari Falcon and a CoCo 3.
Each of these computer platforms could be said to be "crazy" to mess with in this day and age and of course we have our Modern MacOS X machines and Windows or Linux desktops for our day to day work (or for compatibility to the corporate world).
Yes, we could emulate all these machines and save space on my desktop or in my house, but the reason I use the original hardware is for me there is just no equal no matter how close the emulation comes to working with the actual hardware.
Of note, since I have always been big into music, the only application that keeps me from moving to Linux in iTunes. I love my iPod and have actually thought of keeping a machine just for music for my iPod/iTunes and running Linux for day to day operations. The only real problem is, that I want to limit the number of machines and feel it would be a waste of my Macintosh G4 Mini to relegate it to just doing iTunes/iPod, but maybe a G3 iMac would be okay.
If only I had left my music as MP3s ;-)
Anyhow, I use my retro machines for the games they run best and still feel that of all the machines, The Amiga is definitely one that *could* do what I need done (apart from the iPod/iTunes) and really though it is over 15 years old, still is relevant as a computer. I know guys that are using Apple // series computers today still and again some that even use a C= 64 or 128 for their day to day needs.
This post is getting lengthy, so let me close out by saying something I have always felt: "If your computer does what you need it to do and you are comfortable with using it, then continue to use it!" Why fix it if it ain't broken?