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As of August 2014, it is not possible for a person to upgrade OS 9 to OSX. A person will only be able to upgrade to OS 9. 2.
No it cannot
Windows XP :-)
No Mac OS version can be considered to be in the direct upgrade path, as Mac OS runs only on Macs, and is incompatible with all of the software of Windows 2000.
There are websites that have opportunities to upgrade mac os x 10.5.8 to 10.5.9. These websites can be used for this upgrade purpose. When the download button is clicked, it will do everything automatically.
You will need to purchase a 10.4 (Tiger) disc to upgrade a Mac from 10.2.8.
All Apple is willing to say is "Fall 2014".
yes
Unfortunately No. You should upgrade your OS 9 machine to OS X
Windows XP Professional is an upgrade to Windows 2000 Professional. Windows Server 2003 is an upgrade to Windows 2000 Server.
Only XP and Vista have support for upgrade from OS with maintaining of files. Any OS can do a clean upgrade as long as the Hardware meet the minimum requirements.
You can upgrade OS 9 to 10.0 , 10.1, 10.2, 10.3, Maybe 10.4