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Apple IIgs: 1986
In the mid-80s, the Apple II was still alive and well, especially since Macs were so expensive. The IIgs was an attempt to add some Mac goodness to the II line. It didn't really work. Still, Tim Walker, an Austin Texas-based writer and analyst, recalled "My first Apple was a IIgs that my dad bought for me in high school -- it replaced the TRS-80 (with *two* 5.25" drives) that had sat on my desk for a couple of years. I used it all through high school (graduated in 1990) and halfway through college when I switched to the fancy new Macs in the computer lab at the University of Texas."
Apple IIsi: 1990
This was the first Mac I pesonally owned. It wasn't an especially good model, but it mattered a lot to me. For me it was the computer I used to introduce my daughter to computing. Her grandparents, both now deceased, also recorded stories on it for her and she'd play them often.
Mac SE/30: 1990
Technically speaking, this popular model would have been better for me. Alan Zeichick, long-time technology journalist, editor, and publisher, said, "My first Mac was an SE/30. Loved loved loved that machine, especially after I put in an expansion card and used it to drive a big color monitor." In 1990, with Windows 95 still years away, that was no small matter.