That’s a good point and as you know, that was my own experience a few years ago. However, I don’t think my users (back then) weren’t keen on DC because it was ‘different’, it was because it just wasn’t as slick as it is now (and the other platforms were slicker).
DC today, is a very polished product, and I’m fairly confident it’s reached the point where it can persuade old school forum users that a modern platform like DC is worth the jump - if they give it a fair shot.
I wonder if we skinned Discourse to look somewhat like phpBB if people would actually prefer it. With a lot of Discourse’s features like the live preview when making posts I think that could work.
This is extremely likely to work from what I’ve seen. Looks matter way more than they should!
Decide which of you is the customer in this equation, from what you’ve said thus far it’s you.
Listen to the customer, don’t design by committee and most importantly stick to your guns.
When people have gotten used to a forum working in a particular way (even if you can’t even properly search the forum), the most active users will be against change and the rest will be indifferent. That’s perhaps the biggest challenge: Your most valuable users are most likely to be resistant because if they didn’t like the forum, they wouldn’t be as active as they are. 
We had about 3500 unique weekly users. When we switched from phpBB3 to Discouse it wasn’t overnight. We announced the coming change 1 year ahead and regularly posted about progress with data conversion testing, translations etc. But what we didn’t do was giving our most loyal users a chance to try the new site as it was being prepared.
So during first two weeks with Discourse we had very negative feedback from long-time users who suddenly couldn’t find things and couldn’t understand the new logic. They threw in our face what they thought about new site and left. Of course there were long-time users who didn’t mind the change and figured things out quickly but they didn’t “defend” the new site as loud as other could “attack” it with they negativety. And as active members began to leave there were less interesting discussions and people visited less and less the site as there was nothing to read anymore. Only thing that was keeping us alive was Trading side of the forum. But as we needed users to keep an eye out for others to follow trading rules (to avoid scams), there was suddenly nobody to help us to moderate the trading forum.
Don’t get me wrong … I really love Discourse. When starting new forum I woldn’t hesitate to go with it. It’s just wasn’t smart move from our part to switch like we did … something should have been done differently 
We have actually skinned Discourse to look more like phpBB for a customer in the past, check out
I personally feel like it’s better to move away from the old forum look, but I can understand not wanting to scare off users who can be put-off by big changes.
Wow - right down to the signature prosilver font families? Damn, that does look pretty close to the real thing.
I mean, my “stubborn” admin isn’t so stubborn anymore now. After installing a lot of plugins, setting the default view to “Categories+Latest,” renaming “Uncategorized” to “General Discussion,” disabling the narrative bot, integrating our discord server, and doing a few CSS overrides to fix up some weirdness with certain plugins and our dark theme, he actually doesn’t seem to mind it.
As for the rest of our team, everyone’s adopting it pretty well and we’re even coming up with ideas on how we could theoretically use things like the Babble plugin to provide a better link between the forum and our Discord (though, not sure if that can be done.)
Did you see this?
Nope, I didn’t. Though we were thinking more of a bridge between Babble and Discord so that you could enter a specific category and chat with people on Discord through the Discourse UI (for example, if you don’t qwant to use Discord directly or it’s blocked like it is at my school.)
That way you can still do IM with the rest of the community, it’s not dependent on what IM protocol you use. Discord users will see Babble messages and vice versa.
I really don’t recommend that. At some point you’ll wonder why it is that you can’t change stuff about the category. I’d recommend creating “general discussion” and disabling uncategorized.
Huh, never thought about that. Though it does seem to work for now and it makes him happy. Maybe I’ll slip the change in while he’s asleep, mwahahaha.
I wrote this thing last year which might be helpful: It’s Time We Talked About Tags