...should I buy a new version?
Current version is 14 (CS4).
To answer your questions, you cannot install Illustrator 8 on iMac 2009 since that old version was made for the old Mac OS 8-9 systems. Intel Macs run OS X 10.5 and higher. The last version of OS X was 10.4 that supported those programs that ran in the "Classic" system emulator on the PowerPC processor Macs. Since the Intel processor Macs came out, OS 8-9 "Classic" system programs were not supported and "Classic" is not and will not be made available to run old programs.You can get the SheepSaver emulator that will run under OS X 10.5 Leopard and run your "Classic" program but I have not used it and it would be a bit flaky in the stability area, from my understanding.
So in essence you have to upgrade.
Now, since Adobe doesn't have the liberal upgrade policies like in the past, you can't directly upgrade to Illustrator CS4 from 8.0. You need CS1 to be eligible to upgrade. In that case, you will have to get a copy of Illustrator CS1 Upgrade from a 3rd party, like on eBay or Lemswap Group on Google. Then you can register that and get on the upgrade path to CS4 Upgrade. Adobe is very good at allowing you to do this. I can explain further how to purchase software on eBay, I've done it for years safely and upgraded that way and saved lots of money as long as you take precautions while doing it.
Or bite the bullet and get CS4 non-upgrade.
Even if you could somehow get 8.0.1 working on your new iMac, your capabilities would be limited. Moreover, if you think you'd be exchanging files with others, you'll find yourself in impossible situations.
Really, both the long and short answer is 'buy a new version.'
Thx for the update, I'll appreciated your help and time to let me know more about adobe illustrator.
Thx for the update, I'll appreciated your time and help to let me know more about adobe illustrator.