First Apple product for my own use was an unenhanced 512k Macintosh in late 1985. Minute I unboxed the thing and booted it I knew I was done buying DOS machines even if I had a few of them around for another couple years.
First gear I ever bought from Apple was an Apple IIc in summer of 1984 for a nephew. He was a farmer's kid then, and has since credited that machine for his eventually having become an aeronautical engineer. I credit that more to his self discipline, and his fervent desire to do something besides help a cow dog fetch a bunch of wandering Holsteins down off a hill farm's pastures on chilly summer evenings, never mind shovel out from behind them in the barns.
The first product I owned was an iPhone 4 (that my mother gave me), that's when I discovered Apple, but the first Apple product I buyed myself was an iMac 20" Early 2006, after two years of messing around with hackintosh (even tho I'm back at it haha)
Then business pushed me to these newfangled PC's, learning DOS 3.1, basic, WordPerfect, Lotus 123, and of course DBase II where if you wanted a database, dot prompt...start typing. AppleWorks was so far advanced, but there was the business adage "No one ever got fired for buying IBM." Built my own PCs (not laptops) from 286 processor on.
Finally, while already had iPhone and iPad, Windows 8 drove me back to Apple as I needed a laptop. After trying a Windows 8 laptop, returned it to Best Buy and got a MBP.