Hi, I am the part of @chibititan working on this. To answer your first question, I've been going pretty heavy on the learning but only for about 3-4 weeks now.
Since I gave up on the rigging add-ons I have fully embraced building custom armatures now. The more I learn the more I like it. I have seen that Ian Hubert video. I like his videos a lot but have really heavily been leaning on these tutorials for a lot of stuff now. Also very short and to the point.
In the second picture above, basiaclly all those colored bones you see are IK controls. It really does make things nicer. I still have a lot to learn about actually building out the animations and that run cycle could certainly use more work but I'll get there. :)
After trying multiple ways of weight painting, I did give that voxel heat add-on a shot and I really like it quite a bit. It isn't exactly perfect. You still have to paint some weights and do some clean up, but it really does save some time in the end. And it adds some functionality I found very useful that I don't think is available in base Blender. Like you can actually say, only allow x amount of bones to have a vertex. Like if you only want a single bone per vertex to start before painting, you can make it do that. Or another useful one is you can select vertices and tell it not to change the weights on those vertices. I used this when I rebuilt the hands armatures after I had already fixed all the weights in the body and such. I was able to preserver those and only remap the hands with the add-on, then do the touch ups in paint mode. It likely saved me hours.
I don't mind you chiming in at all! I appreciate it very much actually. Always great to hear from a fellow Blender learner.
Yep you're going through the same sort of steps as me, sometimes it can be tempting to just rely on addons or even paid plugins etc. as shortcuts but those only really work to begin with until you have a solid grasp on the fundamentals like with everything. It's nice I guess to know I'm not the only one as I'm largely self-taught through tutorials etc. on this, same goes for programming and everything.
You are definitely not alone. 😀 Self taught is the best! Really shows the desire to learn is there. Though yeah... really tempting to take shortcuts that often end up being a waste of time sadly.