I'd much rather see a drop-down that lets the user select the format they were writing, and "Classic PM" would be one of the options, along with Markdown, and maybe WSYIWYG. The default would come from user settings. The database table would consist of "ContentType" and "Content", and ContentType would select the rendering module which converts it to HTML, then you cache that in a separate layer. This is how many content systems work, including Drupal.
This way you have the option to go back and re-render everything to handle new ideas for site design that depend on changes to the tags, and you leave everyone with the ability to continue to edit their posts from before the cutover.
The entirety of the rendering for old PM format should be bundled up into a module and given unit tests. It's more effort, but I strongly feel this is the "right way" to handle it.
It also lets you iterate on Markdown rendering, later. You could internally have formats like "text/markdown-2024" and "text/markdown-2027" and show them to the user as simply "Markdown" while using the specific type stored in the table to keep rendering the content with the same renderer as it was written, so that new Markdown implementations don't break historic rendering.
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