David Shuman wrote:
It appears there are issues and processes that require
the maintenance of config files and the like after an upgrade of OpenBSD. As I am relatively new to this
process I intend to create two directories in my home
directory to keep copies of all my alterations to OpenBSD. I hope these will assist me in the upgrade process and protect me from loss of data/etc as I understand the home directories are protected from
changes during the recovery process.  If anyone
can point out the limitations or additional
considerations related to this process I would appreciate the guidance. (I have made some
significant post install changes to Comixwall that
was based on OpenBSD 4.3 a while ago.  However,
I have never seriously considered assuring I could
upgrade an OpenBSD system. As I am now considering significant and long term use I need to plan for this event.)

One directory will contain modifications
/home/{userid}/chgusr      where
/home/{userid}/chgusr/etc/rc.local
     {80x50 console changes)
/home/{userid}/chgusr/etc/X11/xorg.conf
     {modified due to difficult hardware)

Another directory will contain additions
/home/{userid}/addusr (djbdns a bind replacement may be in here) where the subdirectories are the locations the content was added to OpenBSD. I am hoping this content can be copied after an update as it is not a part of OpenBSD making upgrades
easier for me.

Thanks for considering and assisting in advance.


read http://www.openbsd.org/faq/upgrade44.html
This page describes 4.3 -> 4.4 upgrade (Not re-install)

tar czvpf etc43.tar.gz /etc
tar czvpf home43.tar.gz /home
tar czvpf my_wierd_program_binaries.tar.gz "insert list of this stuff, if any"

sftp
or
mkisofs
cdio -f
whatever, to get off of computer completely if you can't lose this stuff.
You are doing this anyway regularly. Right!?

wonderful sysmerge will drag you through full list of stuff it wants to change, letting you control all of it.

--
A human being should be able to change a diaper, plan an invasion,
butcher a hog, conn a ship, design a building, write a sonnet, balance
accounts, build a wall, set a bone, comfort the dying, take orders,
give orders, cooperate, act alone, solve equations, analyze a new
problem, pitch manure, program a computer, cook a tasty meal, fight
efficiently, die gallantly. Specialization is for insects.
  -- Robert Heinlein

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