As you can see below from my March 31 post, my last attempt to upgrade failed. Thanks to charos and geoff for their suggestions. Maybe it was too late but running xdragon didn't help and my octopus name is still the default.
Anyway, I restored the entire Linode from backup so am still running BOA 2.1.3 which is screaming for updates. Obviously I'm hesitant to upgrade BOA beyond 2.1 given my experience but I'm confused by this statement:
"These special 'legacy' commands allow you to install and/or upgrade the 'old stable', once the 'new stable' is released. But only until another 'stable' is released, of course."
This implies that it's too late to use the "up-legacy" commands given there has been additional releases since 2.1.3. Is this true or am I over-thinking?
Also, Given my Linode is Debian 6 64 (3.14.4) and all my sites are using Drupal 7.26, MariaDB (5.5.36) and PHP 5.3.28 I still don't understand why the "stable" upgrade had issues. Been using BOA for over 2 years and all prior upgrades were flawless. So, I'm considering creating another Linode, doing a fresh BOA install of latest stable and migrating the sites between servers.
Is this the best approach, or should I go boldly forth and try the normal upgrade again?
As ever, thanks for your responses.

Comments
Best way to keep your Debian up to date
is to install latest stable + backports.
Once you install your vanilla Debian 7 do this:
nano /etc/apt/sources.list
your source list should look like this:
http://imgur.com/SrQg0yD
you can also add to the last line contrib and non-free, but since you are using a server only better keep it as simple as possible, but it is up to you, no problem if you add those lines.
I would leave all the crap behind and start fresh on a new Linode.
BTW I do not use Linode, I used vncviewer to get into the server side of my VM, check with Linode how to edit your /etc/apt/sources.list.
Once another stable is released you just change names in your file.
BTW Debian is going LTS, bye bye Ubuntu.
Legacy is still at 2.1.3
There is no 2.3.x release yet, so the legacy mode still points to 2.1.3 as listed in the changelog: https://github.com/omega8cc/boa/blob/master/CHANGELOG.txt#L266
You should try upgrade to latest stable again. We did this even on some very old test images and there were literally no issues.
Obviously, there is no guarantee, but for any BOA instance properly managed via BOA scripts and w/o dangerous tricks, like modifying /etc/apt/sources.list manually, it should just work.
We maintain literally thousands of BOA instances using totally automated upgrade schedules, and they all (including some remotely maintained Ubuntu instances) were upgraded from 2.1 to 2.2 w/o any single issue, automatically.
Dangerous tricks?
To add the backports line is standard Debian practice, then apticron manages the update/upgrade.
Anyway, to each his own, I am glad that my post prompted you to reply.
It is a wrong practice to
It is a wrong practice to manually edit /etc/apt/sources.list or anything related to packages sources when you use BOA system, because your are making it effectively non-supported with potentially unexpected side effects and conflicts, but it was the original question above and not your bad advice what "prompted" my answer, obviously. I hope this clarifies any doubts.
Wrong practice?
The idea behind backports is to enable a smooth transition to next stable version.
I don't think that any of your automated scripts does that.
So, unless you prove me wrong I will continue to be "unsupported", which I already was, so don't really care.
Thanks to all for the advice
I'll try another upgrade after taking a snapshot of the Linode. I've never strayed from just applying the BOA scripts so should be good. Given my cautious nature I'll do it in two stages: "legacy" first then latest stable.
ckosloff, I'm pretty much a Debian white-belt so until now have never heard of backports. Yet another thing to learn. I'll educate myself. Thanks for the feedback.
Be scared, be VERY scared
That is pretty much what omega8cc is saying for anything that strays from their automated scripts.
Backports are not my invention, more info at backports@debian.org.
They are a bridge between two stable versions, so there cannot be any problem there, I have had this setup since I started out with BOA.
You have to understand that Debian has 4 branches: stable, testing, unstable, and experimental.
Testing is the next version of Debian, as the name implies it is being tested, usually not recommended for servers, although some ultra-geeks like to play on the edge, I use it on my desktops.
When an update in testing is deemed too important to be left to the next stable, it is ported to the earlier stable, hence the name "backports", with backports you are still in a stable version, so I don't understand why all the fuss about it.
Plus it ensures a smooth transition to next stable, you don't have to deal with "dangerous" version changes.
Omega8cc's contention that it is a dangerous trick is ridiculous, they think that they can control the flow of Debian development from their scripts.
Debian developers don't know about BOA, omega8cc, etc. and you can imagine what they would do with their comments.
docs/UPGRADE.txt
Also, make sure to actually read and follow: https://github.com/omega8cc/boa/blob/master/docs/UPGRADE.txt#L6