I wonder if Apploetalk has anything to do with it?
OSX.4.x lost the file transfer ability of Appletalk... 10.1.5 thru 10.3.9 had it!
http://docs.info.apple.com/article.html?artnum=301183
With OS9 set with Appletalk to using TCP/IP, and or Chooser>AppleShare+IP, you can connect to the 10.4.8 machine.
Another solution is OpenDoor's $39 Shareway IP, (some OS7, 8, 9 releases had a limited version included)...
http://www.opendoor.com/shareway/
Which makes OS9 Tiger compatable.
"Mac OS X 10.4 and later don't support Personal File Sharing (or other AFP) over Appletalk, though by initiating the connection from the opposite direction you could still achieve an IP connection from a Mac OS 8 computer to a sharing Mac OS X computer. The Network preference pane in Mac OS X 10.4 and later still offers the AppleTalk checkbox, but it is for browsing AppleTalk-advertised resources and zones. The subsequent connection must be over TCP/IP."
http://docs.info.apple.com/article.html?artnum=106461
For 10.7 & up, likely this applies...
Connecting to legacy AFP services - Apple Support
And lately Apple has dropped AFP totally, SMB is used... & perhaps a solution here?