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I think if you try to continue along these lines you are going to be in all sorts of pain!
You can't replace your RH 4.6 while it is running the computer. The usual thing is to boot off an installation CD so you are running the copy of linux on the CD. Then you can overwrite anything on the disk with impunity.
So if you want to use your CD you will need to have a CD drive attached and set as the boot device in the BIOS menu.
It's almost certainly better to do a fresh install than try an upgrade, especially skipping multiple versions. Is there personal/non-system stuff on the disk and can you back it up somewhere?
Sorry if I have misunderstood what you are proposing - but it doesn't look very promising
Doing an install without physical access is a very dangerous business unless you have something like an IP KVM + remote power control or a full featured IPMI/Lights Out Management system on the server. You could do a hard drive install, but for things like this I generally just use pxelinux to PXE boot the installation kernel and load the initrd with Anaconda (yes -- Anaconda is the install program), but again without physical access or its moral equivalent, this is very dangerous and it's very possible to screw up in such a way that you can't recover.
The install disk should be bootable, and yes, you just need to pop it into the drive, boot (assuming the machine is set to boot off the CD), and go.
Since you haven't touched a Linux system in a long time, I would definitely ask for help from the sys admin group, particularly if the server contains mission critical data. If there's anything important at all on it, you really need to back up before you start. In theory, an upgrade should be non-destructive, but things can and do go wrong. Oh yes, and do remember to test your back-ups before you start. In general, though, if you feel unsure about this it's best to let someone more knowledgeable help.
If the ISO file was downloaded from the RHN website then it is bootable but not the point here unfortunately.
In your specific case I would lean towards asking the sysadmin group to help you on this, upgrading using the iso image would be too dangerous and the risks are high. As mentionned before you _may_ want a backup of the existing data if they are critical.
In the case of an update (4.x to 4.x+1) rather than an upgrade (4 to 5), I have done it several times remotely over the console, it save me from asking the sysadmins who are in a different location.
I am happy to document the procedure if you want it for later use, just shout.
Ok,  and  describe a CentOS remote instalation, this is definitely applicable in your case. Obviously you need to point to the install media.
I will try to do it as well, i want to see how it works too now
ok, it's been a while and you may have moved on but I never quite managed to get it to work that way.
anaconda docs says it can boot from hdd but i have not yet managed to get to behave in a stable way.
do you have access to another box? I am thinking either:
1- create a separate installation server with Cobbler/koan or a simple NFS server then I can help more
2- ask the sysadmin to do it for you even if it's a PITA