Otto,
Anyone who jumps into web programming, whether they're a Harbour programmer or not, goes through a learning process and gains experience day by day. Everyone finds their own way.
Thinking there’s one right, foolproof way is a fantasy, even outside the Harbour world, nobody has that. There are tons of architectures, methods, patterns… and over time you pick things up and absorb what works for you.
Your concern is understandable, but it’s something that’ll probably weigh more on you than on other users, depending on how you build your solution, your tools, servers, languages, and so on.
Setting up your environment, like with Cloudflare, isn’t the only option. For example, HIX can be used in different ways, though lately Cloudflare has gained traction because it’s easy and offers some advantages.
If you have your own way of setting things up, what you could do, if you want, is explain it clearly so others can understand, and maybe more help and guides will come from the community over time 
Can we create a guide focused on CF tunnels? Yes, but without forgetting there are other options. And also keeping in mind that setting up CF for something like HIX isn’t the same as configuring apache, php, node, etc..., each stack has its own setup.
In the last webinar, I already explained how Cloudflare tunnels work, and since then I’ve been glad to see different users trying it out. These days there are plenty of Cloudflare tutorials that explain it well in different ways, and you can always ask questions in the forum. If you need or want to, you can post the presentations here again. I think it helped more than one person understand it properly. Once you grasp the concept, you can then look for more information if you wish.
Little by little, things will change, as someone here says... the flow!
C.