I had been using a lab of Classics with system 6 on a MacJANET network for a bit in school, and when I bought my first Mac (a IIsi) it came with 7.1. I eventually got 7.5 through the old "my Performa didn't come with disks, please mail them" trick, and took that right up to 7.5.5 downloading the updates on my dad's 486 and transferring over disk. Once I got online with a 28.8 global village modem (going away gift when I moved) I got into 7.6.1. I desperately wanted to run OS8 and even spent may sleepless nights trying to hack apart system files and staring at lines of gibberish, but the best I could ever do was just mimic the look. Eventually I was given a 6320 and ran 8.6 for a bit but this was around the time 9 was out so I switched over pretty quick.

System 6 with multifinder was pretty neat, my friend had an SE dual floppy that ran it for quite some time. I consider myself a System 7 child as that is what I had used the longest.