Well, this is an upgrade of a more than 10 years old code, quite a journey.
Since you are on oracle, then the stepwise upgrade to 5.8 is not necessary (concerns mostly the upgrade scripts) up to my knowledge - but i have no Oracle installation. For Oracle the upgrade scripts are maintained by best effort, so don't not expect a fully paved road. Brian Fenton has upgraded a Oracle-OpenACS site to OpenACS 5.9.0, the necessary fixes for that are included in 5.9.1.
The red in the compatibility matrix means "don't run a site with this version", if something is broke, there will be no fixes for this version. For example, there is a bug in older versions of AOLserver (including at least 4.5.0), where "funny characters" might show up, this is for e.g. the upgrade process not relevant. Also concerning XOTcl, i would not be concerned, when you do not use XOTcl packages.
Since on Oracle, I would try the following:
a) prepare
- Get everything compiled for the new NaviServer,
- Make configurations in the openacs-config file coming for NaviServer (don't expect, the old AOLserver config file will work)
- make a copy of your existing OpenACS tree (such you can
quickly switch to the old version, in case the upgrade does not work, will take longer)
- since you are on CVS, get openacs-5-9-1 of OpenACS and merge local changes, if these exists ("cvs ... upgrade -r ..." will do this, conflicts might show up)
b) backup and boot new version
- shutdown your old instance
- backup everything (DB + OpenACS tree)
- start the new server - it should boot up sufficiently well to get to the upgrade scripts
c) run upgrade scripts
- first OpenACS core packages
- then application packages
This recommendation is on weak grounds, since we have no Oracle experiences.