I think that when it comes to business what a lot of companies don’t understand (and in this case, using your example of the small vs big fish), is that small fish x500 is better than no fish.
And some of those small fish (fishes?) will become medium or even big fish. It’s an investment if CDCK wants to allow support. Also, when it comes to support, it can always be limited as it is now. Community support for lower plans, limited custom support to medium plans, priority support for higher plans.
And finally, in this kind of product/service, the goal is to make the customer dependent so they won’t leave. If I build a community of 1k people and everything is going great, why would I move everything to a completely new company instead of going from $20 to $50, for example? If I move everything, maybe I will have to pay for that migration service, my members need to learn a new platform (which will eventually make some of them leave the community completely), etc. So by introducing smaller differences in plans and not so tight limitations in page views and emails, the community grows, making it harder for the customer to leave, making it easier to upgrade, step by step, instead of going from $100 to $500 a month.
Yes, self hosting is an option to mitigate this, but then you have to deal with all the issues yourself, you need to either have someone who’s an expert to install and maintain everything, or you have to learn it yourself, which probably 90% of people who want a forum, are not. And maybe the extra you have to pay a developer here and there to fix or update things, is not that different from what you would pay going from $20 to $50 a month (in a year that’s $360 extra). Does it make sense?
My opinions here are more focused on a business plan that allows anyone to install and use Discourse, build a good community, and only focus on that.
As Communiteq very well says on their website:
We think this product is too great to be limited to a technical audience only (…) Choose our Discourse hosting services and never worry about hosting or maintenance. We keep it running — so you can focus on building your community.