Each PCB is a bit of money after all, and if you are inevitably going to make a mistake it's better to breadboard.
But as far as difficulty goes, things like KiCad exist for a reason. Computer automation and checks help, as well as parts libraries for you to download/copy rather than building your own footprints.
So feel free to start KiCad + ordering boards the moment you are willing to lose money on your mistakes!!! It's not any harder IMO. Just costlier.
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As far as learning Kiad, this guide is good but it's missing the broad overview IMO. So here's my broad overview:
1. Build symbols representing each chip or part you plan to use. Standard parts (like resistors) already exist in KiCAD7.0 library, but inevitably there will be a few missing parts for your project. This may be called symbol editing, but perhaps it's more accurate to call it pin-naming.
2. Hook up the parts together in the schematic editor. Double check symbols and their pinouts now. Fix symbol mistakes now. This creates a computerized set of nets (connections) that KiCad will try to enforce moving forward.
3. Choose the footprints for every part in your schematic. Beginners should probably use 0805 (inches) parts or larger. (equivalent to 2012 metric). Like #1, there is a footprint library for common parts, but you will inevitably have to create at least one or two footprints of your own for your personal projects. Footprints tell KiCad where pins are located physically (inches or mm) here vs there.
4. PCB layout begins. KiCad has a 'rats nest' based on your schematic. As long as #1, #2, and #3 are correct (ie: correct symbols / pinouts, correct schematic, and finally correct footprints) you probably can't make a mistake anymore. Assuming a low speed beginner circuit anyway (the professional would focus on physical issues like heat, noise, EMI, crosstalk and other such issues. Beginners can likely ignore all of that assuming you chose a suitable beginner project).
By step#4, KiCAD knows the name of every pin (#1), which pins should be connected to which pins (#2), and where each pin is located physically (#3). All that's left to do is draw your wires together in step#4.