I have a technically ancient site built with Plone 2.1. Yes, it dates back to 2005. Because of all sorts of complications I never bothered to upgrade it. It still runs fine, so compliments to the durability of Plone
The time has come to face the inevitable: upgrade my site to the current Plone 5.2. I can think of two approaches:
Setup a series of Plones to go through all of the intermediate regular migration steps (2.1 > 2.5 > 3.0 > 3.2 > 4.0 > 5.0 > 5.2 and what have you).
Setup a fresh new Plone 5.2 and somehow import the content of the old site
My site is pretty much a static text site and contains only a hierarchy of folders with pages. It uses the 2.0 style of related pages, wich was based on keywords. Other than standard Plone functionality (sitemap, search, navigation tree) there are no bells and whistles. User accounts are no issue, one editor account as owner of the new content is fine.
Because of the simple content, I'm inclined to think that importing the content (from HTML if needs be) in a fresh Plone 5.2 is the best approach. I'm comfortable with programming in Python 3. I'll learn Diazo to recreate my site's theme.
How would you approach such an upgrade? Any advice?
For such a long jump in versions, I think transmogrifier is the best way. Add collective.jsonify in your Plone 2.1 site. I hope this works, otherwise maybe upgrade to 2.5. Create a json export with this, and import it in Plone 5.2 on Python 3. That is the short version.
Best information is at https://training.plone.org/5/transmogrifier/index.html
[Confession time: I still have a Plone 2.5 site, which I want to migrate in the same way.]
I can confirm that exporting data with collective.jsonify (you have to use an old version) works for a Plone 2.0 site. We just did this for a client.
Old Plone versions do not even use buildout, so adding collective.jsonify might require some ancient Python and Plone knowledge but it is definitely possible (took us two people and something like 45 min to figure out all the quirks).
I would strongly recommend to use transmogrifier for such a large upgrade step.
