[gentoo-server] Challenging Update Question

[Collin Starkweather <gentoo@collinstarkweather.com>]

I have a server that is in need of a significant update, but it's  
proving a challenge.  I have a big picture question, then provide some  
details below.

(I originally thought the gentoo-admin list would be the best place to  
ask this, but based on the stats, it seems to be relatively inactive.   
Let me know if there is a better list to ask the question on.)

Please excuse the length of the question, but as you can see, there  
are a variety of variables in play.

The Big Picture
---------------

The server has not been updated since late 2005 or so.  It just runs  
Apache, mod_perl, and an application server.  So far, it has just  
hummed along doing its work without complaint, solid as a rock, which  
is why no one has bothered with it.

As you doubtless know, if you miss a couple of upgrade cycles with  
Gentoo, there can be (and has been) breakage when trying to emerge -u  
world.

There are two identical drives, and I've mirrored (manually, not RAID)  
one onto the other.

The challenge is that the box is in the U.S. and I live in China.   
There is no one there who can administer it; however, if something  
goes really wrong, someone can just swap the drives and reboot.  The  
key factor is that I want this to be as low-risk as possible since  
swapping the drives is about the extent of on-site support available.

The big picture question:  Would it (1) be simpler and easier to  
rebuild from scratch on the redundant drive, or (2) is it simpler and  
easier to deal with the current issues updating from 2005.0 and a  
2.4.x kernel?

The Details
-----------

Option (1):  Rebuilding on the Redundant Drive

Pros -- It seems this would be the easiest way to do things, and I get  
a fresh kernel and build.

Cons -- If I rebuild on the redundant drive, I lose the ability to  
swap drives if there is breakage.  Also, the application server  
(Apache Pagekit) is solid as a rock, but a real bitch to configure.   
Last time I tried to upgrade Pagekit, due to Apache versioning issues,  
configuration changes, etc., it took me a full weekend.  Not fun.

Option (2):  Upgrading from 2005.0

Pros -- Perhaps less risky (advice on this would be appreciated!) and  
I maintain another drive I can use to compare configurations,  
selectively roll things back, etc.

Cons -- The gory details.  When I did an emerge --sync, the  
/etc/make.profile symlink broke.  It used to point at

   /usr/portage/profiles/default-linux/x86/no-nptl/2.4

which no longer exists, I suppose since the 2.4.x kernels seem to no  
longer be supported.

So the questions that arise are:

1) Would it be less risky to upgrade from 2005.0 to 2007.0 than  
rebuild from scratch on the redundant drive?
2) What is no-nptl?  I don't know why the old portage profile was  
/usr/portage/.../no-nptl.  It seems to have something to do with  
glibc-2.4.  Do I still need it?  Or can I just point /etc/make.profile  
at /usr/portage/.../2007.0?
3) I pointed /etc/make.profile at /usr/portage/.../2007.0, and tried  
emerge -pu world.  I was told that mail-mta/qmail no longer existed  
and is required by sudo (?!?) which is required by libapreq2.  Perhaps  
mail-mta/netqmail is the new qmail?  Anyway, this gives me the  
impression that there are deep dependencies that may have changed  
significantly.  Is this what you would (subjectively) characterize as  
a bad sign?
4) What would be the best order of operations?  emerge -u world, then  
update the kernel, or update the kernel, then emerge -u world?
5) 2008.0 is due on March 17.  Is it worthwhile putting off the  
upgrade for 2008.0?  I wouldn't want to deal with two difficult  
upgrades if there is breakage between 2007.0 and 2008.0.

Thanks in advance,

-Collin

-- 
Collin Starkweather, Ph.D.
http://www.linkedin.com/in/collinstarkweather

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