I just did an OS upgrade on a 280 (I installed OS 8), so I can relate.  I have a
B&W G3, so a serial Appletalk connection was not an option without spending a lot
of money on a USB-serial adapter that supported Appletalk.

    My solution was to cave in and buy a dock.  A local retailer sold me the old,
original, Dock 1 for about $60.  I dropped an old NuBus ethernet card in (you can
get them really cheap if you do a little bargain hunting.  Mine was a free loaner,
but I have seen them in the Twin Cities for $20 or $30).  An old monitor from the
keyboard and I was ready to go!
    Once I had a 10Base-T Ethernet connection going, Appletalk screamed along!  I
was even able to connect to my DSL router and pull files from the internet at high
speeds.
    I turned on sharing on both machines, then mounted and image of my entire Duo
drive (240 MB) on my G3 desktop, and just made a backup of the whole thing on my G3
drive.
    Next, I popped in the OS 8 disk on the G3's CD drive, and shared it.  I ran up
to the other room, mounted the CD on the Duo desktop, and fired away.  It worked
like a champ.

I can't reccomend using some kind of Ethernet connection highly enough.

On the other hand, if you have an "beige" Mac to connect to, you can do all of this
a lot cheaper (but slower) with just a printer cable.

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