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Desqview, swapping between GoldEd and the BBS watching the users playing LoRD and other games. And before that, scrambling to quit my game and get the BBS back up when I was using my 286 for gaming instead of leaving the BBS running.
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Those terrible, terrible CGA games that I played because for a couple years, I only had CGA and no EGA. The high pitched whine of the CGA monitor whenever I stood behind it.
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When I finally got OS/2, and could play Descent or Doom, while the BBS was handling a phone call in the background.
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Even older, printing out yet another Bill the Cat on my dot matrix printer.
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Typing in games from Compute Magazine into my Atari 130xe, but the checksum being wrong because I used abbreviated basic commands due to being a lazy typist.
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Getting killed by that darn Terminator in Zone 2 of LOD again...
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Going to my Uncle's house to transfer all of Kings Quest 6 from 1.44mb to 1.2mb floppies.
retrocomputing
Discussions on vintage and retrocomputing
To add devices for your computer (like a disk drive, a serial or parallel port, or more memory) you needed a huge box with a very rigid cable and a lot of space.
This was for the TI-99/4A.
I remember mom setting me up with my own 3.5" floppy for all my files. Later on it was CD-RWs for me and my little brother.
Felt like I had more storage than I'd ever know what to do with at the time.
A couple:
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CRC Errors when restoring 9-track tapes (the large reels) on a mini at work.
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A manager not knowing a removable 256meg Disk Pack suffered a heard crash. So he mounted it on 4 or 5 production drives, destroying the hardware. He did this to test if the Disk pack was OK. This caused almost a month of agony while we went looking for hardware to replace the drives. This caused manufacturing to slow down since inventory could not be ordered.
I can almost laugh now :)