I try not to dwell on certain decisions that later turn out to be bad moves, but one that keeps popping up is my insistence on putting a hard disk drive on my Atari 800XL computer.
Let me explain.
Putting a hard disk drive (HDD) on my Atari 800XL was not cheap. It was around $800 back in the 1990s (which is around $1,400 in 2017 money). Contrast that with the Amiga 500 which was released in 1987 at around $699 and it seems like putting a lot of money into old technology. And indeed it was. By the time I'd purchased the Black Box, the cables, and the SCSI drive / enclosure (40MB) it was around $800 for the whole kit. But I was bound and determined, as this was running my BBS and other assorted goodies (terminal program, etc.).
So why the regret? Seems like a pretty cool purchase, right?
Unfortunately I was also going into computer science at the time. And the 8 bit processors were rather long in the tooth by the time I was purchasing said HDD kit. The Atari 800XL also didn't have 80 column screens so I had to use a software-emulated terminal in order to connect to the school's VAX and Sun SPARC station computers. And the C compiler that I had purchased (Deep Blue C) was pretty weak in an era where better compilers existed for the IBM compatible machines (and the Amiga).
So my one regret is not taking that money and plopping it into a 16 bit computer. Who knows if it would have changed my course much? Perhaps I wouldn't have been so eager to get onto Linux when I graduated college. But it's something that pops into my mind from time to time.