Colocated RH8 EOL is a problem. Best course of action?

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I have a colocated Dell 2650 web/webcasting server running very smoothly
with Red Hat 8.0 Professional. The problem is that there will be no more
security updates for it after January.

Obviously, I have to do something about it but the server is on the other
side of town, I can only access it outside my working hours (weekends) or
maybe during the Christmas holiday. A real hassle.

In terms of EOL, I could get RH ES 3.0 with its 5 years EOL or I could get
RH9.0 on it which will be officially supported to April and then community
supported with updates by the Fedora project.

If possible I would like to "upgrade" the OS without actually having to
re-install all the applications & spend a long time tweaking the server to
get it back how it was. I just want to take the path of least resistance
to keep the server running as it is now.

I always keep a complete daily rsync image of the server so I can recover
from any total FS disasters.

1) Can I upgrade to RH 9 reliably without a re-install? I normally like to
clean re-install OS's but this is a special case.

2) Can I upgrade to RH ES 3 without a clean re-install?

3) If I can upgrade, is it possible to upgrade remotely by internet so
that I _only_ need to drive to the other side of town if it all goes
horribly wrong.

+ any other general advise on dealing with this situation.

Thanks


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