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If I accepted having an intermediate jump box, then things go even farther down. Any with a telnet client works, and with something like ZiModem that opens up literally anything with a serial port. I've done "real" work from an Atari 8-bit and Commodore 64 by telnetting to a jumpbox and then sshing into my work Macbook. Spending a whole day that way would be pretty challenging but it could be done. Throw in slack-term and I was able to even keep up with company chat. I was only doing it for fun so I didn't go all the way but I could have set up our g-suite in a terminal IMAP client.
If I accepted having an intermediate jump box, then things go even farther down. Any with a telnet client works, and with something like ZiModem that opens up literally anything with a serial port. I've done "real" work from an Atari 8-bit and Commodore 64 by telnetting to a jumpbox and then sshing into my work Macbook. Spending a whole day that way would be pretty challenging but it could be done. Throw in slack-term and I was able to even keep up with company chat. I was only doing it for fun so I didn't go all the way but I could have set up our g-suite in a terminal IMAP client.
I believe, there are "modern" ssh clients for legacy OSes. A quick google search gave me this SSH client for Mac OS 7/8/9.