This will be a very long reply, but since I feel that we are a bit walking around in circles here, with each person having their own perspective, I decided to just share all my views on this so maybe we can all move on.
I appreciate all of your feedback, though. Some replies pointed me to some good resources, so that’s net positive.
If you have no patience to read it all, I understand it. I just wanted to share everything at once and will probably move on with it.
No, I don’t. Here’s why: if I need to learn XYZ things to make it work, it has nothing to do with an automated system offered by the CDCK team where everything is installed automatically and once you have it installed, most of the support can probably be done via this forum, since we are not dealing with technical issues that are supposed to be taken care by CDCK. So that doesn’t reflect the price structure at all.
There’s a misconception, in my opinion, that has been shared in this topic and I totally disagree: just because I can afford paying $500 a month, has zero correlation to me being an expert and not needing more support than someone who pays $20 a month. Actually, from my own experience, it’s when you don’t have money that you tend to do more research and learn more things. If I know I have X members and Y page views that fit the $20 plan, why would I pay for the $500? So no, being on a lower plan has nothing to do with having the need for more support compared to someone on the $500.
I think that some people here are confused about this and let me give you an example:
There’s a difference between person A buying a cheap Ford vs person B buying a Ferrari. Different products, different quality (at least in theory, if you are paying more), different price. This is not the case with Discourse plans. You are not buying a better product per se. You are buying the same product, with more or fewer limitations. So the real comparison would be person A buying a Ferrari that only goes up to 50KM/h vs person B buying the same Ferrari but can go up to 300KM/h.
The thing is, person A is buying that Ferrari, cheaper, because they don’t want to drive above 50KM/h. They just like the car. Whereas person B wants to race other cars. When you are on the $20 that doesn’t mean that your forum sucks and doesn’t work properly compared to plan $500. It’s still a great product.
My issue, and that is what made me start this topic, is that:
1 - I think that the limitations should be more focused on features, components, plugins, theme, even limited number of categories that can be created, etc, and not on probably one of the main things that a forum needs: traffic (in this case, page views and the emails). Sure, there should be some kind of limit, but controlled by an automated system that analyzes if a forum for example with 10 members and 20 topics, should have 10 million page views and 500k emails being sent a day. That’s obviously ridiculous and something is wrong. When we build a forum, the main goal is to have a lot of interaction and that’s obviously through people jumping from topic to topic, etc, so it’s natural that page views go up. Now if a forum admin has to be constantly worry about the main thing that’s valuable for a community, that to me is a wrong way of doing things (from the CDCK perspective).
Using the car analogy: you can buy a cheaper Ferrari for $10k, but you can only drive 5km a day at a speed of 20KM/h. Makes no sense. It would make sense that the limitations were more related to what the car comes with: maybe without radio, no AC, non-warmed seats, etc.
2 - The difference in plan price is just ridiculous. If I have a community that is growing fast, going from $20 a month to $100 is like paying $500 for food every month and suddenly saying that you are adding a new member to the family and now you are paying x5 times more: $2,500.
Communiteq has plans that let the user grow, one step at a time. Going from $20 to $50, for example. If they can do it and manage it, I would guess that CDCK could as well. I obviously don’t know how both companies work, but that’s just a guess, especially, as I said, when everything is pretty much automated.
So if you “hate” it, that means that probably something is wrong. There’s a difference between hating something because you can’t afford it (that’s on you), and something that doesn’t make sense to most users (that’s on the company). I don’t hate the company Ferrari for making super expensive cars. It’s their product and if I can’t afford it, it’s on me. Now I would hate it if a cheaper Ferrari would cost me $10k and was super limited where I could barely drive it, and if I wanted to have a better car that behaves like a normal car, I would have to pay $1 million. That makes no sense, because the price vs the features are not proportional.
I don’t mind learning stuff. Being serious about having a forum, doesn’t mean I have to know how things work behind the scenes. I can be serious about playing guitar and I can dedicate my whole time being the best guitar player, but that doesn’t mean I need to know how to disassemble a guitar, how it works electronically speaking, etc.
Are you saying that someone who pays $500 a month for the managed hosting is more serious and therefore knows more about the technical side of Discourse than someone who decides to self- host? Because I can be super serious about my forum and pay $500, because that’s my main source of customer support, but someone who self-hosts and pays $20 a month on Digital Ocean and SendGrid, is just doing it for fun. No correlation here either.
I was never against paying for Discourse. I support it. Actually, me being more interested in paying for their plans is more supportive than someone who wants to self-host, right? 
At least I’m giving them $20 a month whereas someone with a self-host forum is paying $0 to CDCK.
So just to be clear: I understand that paying is good. I don’t think the limitations should be focused on page views or emails (even though some kind of system should be in place to control unusual traffic), but instead should be focused on features that can be used/installed. I think that the difference between each plan should be more linear (20-50-100-250-500, for example).
Everything else, if someone wants to self-host and learn more about what happens behind the scenes, great! It just should be clear that not everyone knows how to, or even wants to spend that time doing it. Some people just want to “plug and play” so they can focus on the community itself, not the technical side of things.
And that’s it. I will move on with this. Again, thank you all for sharing your views and perspectives. Even if we disagree, there’s always some parts that can be potentially beneficial.
Thank you!