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Debian stable not booting, freezes

I am attempting to use debian stable as a production server for a 
hosting company that is primarily windows based, in a attempt for 
them to start supporting the open source community and linux itself, 
but am having allot of problems that are only showing the owner that 
"windows is in fact the superior operating system, because I would 
have had this server up days ago" (his words).

For the past few weeks, we have reloaded the server several times 
since for some strange reason any attempt to upgrade the kernel to a 
2.4.x release from the default 2.2.X install kernel couses it to 
either refuse to boot or if it does boot, freeze up the system.

We need a newer kernel version both for security reasons, and the 
fact that the default FD_MAX for the 2.2.x release seems to be 255 
and thus we can get apache to load, it errors out with a error saying 
it can not open any more files.

I run debian (both stable and unstable) on my private network, and I 
have never seen this happen before; Im sick and tired of working on 
this same server for the past weeks, and I have used only stable 
debian standard packages in the installation, I googled and I still 
have no idea what is going on or why.

Has anyone experienced these refusals to boot or the random freezes? 
This is the only OS on the computer in question, a 1ghz Intel p3 with 
512 ram, and the first boot did so like a dream under the 2.2.x 
kernel, but it was simply too old for the needs of the server.

I know I am rambling, sorry about that but I have been up for the 
past 2 days trying to figure this out, if you have ANY input at all 
please do so, I am stumped and this is really making linux look bad 
compared to windows in a server environment, and I think I hate that 
most of all.

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