Honestly, I completely agree with you. I've failed to set up a link more times than I've succeeded. Which is why I finally got fed up and crawled through it 1 painful step at a time!
Thankfully, they have improved some of the wizards. But the whole thing is quite complex. Once you've done it correctly once though, it does actually all make sense. It really doesn't help that they have a tendency to change the names of things and change the layouts and names of the admin dashboard.
Anyway, I've tried to include all of the got-ya's that may catch people out. For me, working out how to stop the system forcing everyone to log in was a significant hurdle.
It took many go's to work everything out but I got there in the end.
Thanks Marcus. Without a doubt, it IS great. And their free tier is very generous.
I've not worked through that scenario I'm afraid. In fact, I only just realised that there are more "modes" to WARP than are immediately obvious if you simply install the client on Windows and turn on the proxy.
I did try to do a login from the WARP client settings. However, I believe that you have to set up the proxy end first.
I think that the way to do that is to use the dashboard's overview page, use the "Get Started" tab and choose " Secure my web traffic from advanced threats". I think but don't actually know for sure, that should create the proxy connection and should allow the WARP client to log into the proxy and so use the enterprise features. Whether that needs a paid tier, I don't know.
I also believe that you can use the WARP client on servers as well for more control than using the cloudflared client. But again, don't quote me on that because I've not even begun to properly look at that.
I'm afraid that you will need to start by reading the WARP advanced documentation that I've linked to.
Oh, and there is also this which sits under "Networks" Manage Tunnels:
Maybe related?
Let us know if you work it out! 
