Transfer files from OS 8.6 to OS 10.5 and printer issue

I am relatively new to the MacOS world, but I am enjoying every minute of it. I recently acquired a new iMac with OS X (10.5) on it. I also have an older Mac that runs OS 8.6 that someone just gave to me. I would love to network the two and share files, but am not sure how to accomplish this. I have a wireless router, with the OS 8.6 Mac plugged in directly via Ethernet, and the iMac connecting via Airport. The Internet works fine on both, but I cannot figure out how to get the two machines to see each other on the network and share files. Any help on this or any pointers of where I could find any help would be appreciated.
Also on this network setup, I have a HP network printer. It is plugged into the router. The OS 8.6 prints fine to it, but the iMac only prints to it if plugged in via Ethernet. If I try to print to it using the Airport, I get a message saying the iMac is unable to communicate w/ the printer. Switch back to Ethernet, and it works fine. Everytime I switch connections, it says something about Appletalk needs to run on this connection and if I want to start it. I answer yes on either connection, yet Airport still isn't working. Any ideas?
Thanks for any help!

I have a similar problem but the issue is between OS 9.1 and OS 10.5.1. I used to be able to network the two machines using OS 10.4. Clearly something has changed with OS 10.5. I know that 10.5 no longer supports OS 9. In my mind, that shouldn't make any difference. I should be able to network with any machine. I can use the network utility and "Ping" the OS 9.1 machine which means I can "see" it through the network. When it comes to attempting to connect with the OS 9.1 device, I get an error code -41 that says for me to check with the system administrator (me)..
I've gotten to the point where I either get a new computer or I find an answer. I have asked a friend of mine who is a former Apple software guru. I'll let you know if I get an answer that works...

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