* Even though it’s just plain text files, I’ve been unable to move it to another server (you can’t just copy the folder because of its indexing system). There’s more to it.
* It’s somewhat difficult to update and requires frequent security updates
* It’s design, and all the available templates I’ve found look pretty old
* It’s native format is not MD
Not true. Being portable from server to server (even across different file and operating systems) is one of DokuWiki's main goals. All you may have to do is clear the cache. See https://www.dokuwiki.org/faq:servermove
It’s somewhat difficult to update and requires frequent security updates
DokuWiki releases come out like every 1 to 2 years. Security hotfixes are rare but always easy to apply (usually you just replace one or two files). Upgrading is more or less a couple of clicks when using the upgrade plugin: https://www.dokuwiki.org/plugin:upgrade
It’s design, and all the available templates I’ve found look pretty old
I guess that's up to personal preference. Personally I'm still happy with the default template but people seem to like the bootstrap3 and argon templates
It’s native format is not MD
True. There are plugins that add MD support, but I agree, native DokuWiki syntax is much better supported. If you're familiar with Markdown, it won't be hard to pick up DokuWiki syntax, but yeah it's different. DokuWiki is about as old as Markdown, when it was invented markdown was just another unknown formatting language...
Not true. Being portable from server to server (even across different file and operating systems) is one of DokuWiki's main goals.
I've been using DokuWiki for more than 20 years (it's still live on my website though I haven't written new notes in it for more than 10 years). I wonder if the fact that I started with a version 20 years old is a factor. I have done a lot of upgrades over the years, but I started with a much older version. I've tried following your directions for moving the server and clearing the cache. For whatever reason this hasn't worked for me, yet.
Security hotfixes are rare but always easy to apply (usually you just replace one or two files).
One of my most popular pages is a set of instructions I wrote on how to apply DokuWiki upgrades. Not all of your users find it as easy as you do or I suspect my page wouldn't be very popular. If it's true that you can just replace a file or two, I'm certainly doing it the hard way. My instructions include copying all of its files over the old installation.
https://www.joeldare.com/wiki/upgrading_dokuwiki
Anyway, I'm not trying to beat up DokuWiki. It's a free tool that worked very well for me for a long time and I appreciate you for it. It's just no longer the tool of choice for me for the reasons I outlined above.
Look and feel: agree, the default does it no favours (and I wish they'd update their website too, the 1990's look really runs behind the capabilities of the system) - but I've installed bootstrap and then modified to make it cleaner, which was again very easy, just some CSS.